Supporting Information for
Investigations of the Mechanism of the “Proline Effect” in Tandem Mass Spectrometry Experiments:
The “Pipecolic Acid Effect”.
I.Tables S1.Total electronic energies, thermal corrections and 298 K enthalpies (Hartrees) for various conformations of 5-10.
II.Figures S1-S6:Low-energy Structures for neutral, protonated and deprotonated 5-10
III.Gaussian Archive files for structures shown in Figures S1-S6
IV.Figures S7 and S8: Tandem MS for AAAXA (X=Aze, Pip) and AGXGA (X= Aze, Pro, Pip, NMeA)
I.Table S1. Total electronic energies, thermal corrections and 298 K enthalpies (Hartrees) for various conformations of 5-10.
5 / Eelectronic / Therm. Corr. / H298ac-azet11
ac-azet4
ac-azet10
ac-azet21
ac-azet17
ac-azet1
ac-azet26
ac-azet29 / -514.6419834
-514.6419833
-514.6361542
-514.635700
-514.6356974
-514.6354757
-514.6347824
-514.6261769 / 0.163571
0.163572
0.163501
0.163285
0.163283
0.163443
0.163469
0.162973 / -514.4784124
-514.4784113
-514.4726532
-514.472415
-514.4724144
-514.4720327
-514.4713134
-514.4632039
5H+ (O) / Eelectronic / Therm. Corr. / H298
ac-azet_oprot7
ac-azet_oprot2
ac-azet_oprot29
ac-azet_oprot1
ac-azet_oprot8
ac-azet_oprot15
ac-azet_oprot17
ac-azet_oprot16
ac-azet_oprot10
ac-azet_oprot3
ac-azet_oprot12 / -515.0013348
-515.0013353
-514.9954019
-514.9954021
-514.9942444
-514.9940137
-514.9912198
-514.990149
-514.9900973
-514.9825891
-514.9813195 / 0.176519
0.17652
0.176583
0.176584
0.176602
0.176472
0.176453
0.176557
0.176635
0.176264
0.176261 / -514.8248158
-514.8248153
-514.8188189
-514.8188181
-514.8176424
-514.8175417
-514.8147668
-514.813592
-514.8134623
-514.8063251
-514.8050585
5H+ (N) / Eelectronic / Therm. Corr. / H298
ac_azet_nprot17
ac_azet_nprot10
ac_azet_nprot29
ac_azet_nprot4
ac_azet_nprot26
ac_azet_nprot1 / -514.9784677
-514.9698597
-514.9663047
-514.9663012
-514.9642349
-514.9631612 / 0.176603
0.176778
0.176288
0.176285
0.176533
0.176631 / -514.8018647
-514.7930817
-514.7900167
-514.7900162
-514.7877019
-514.7865302
6 / Eelectronic / Therm. Corr. / H298
stump 1
ac-pro150
ac-pro184
ac-pro1
ac-pro3
ac-pro4 / -553.9955582
-553.9885207
-553.9756897
-553.9749671
-553.9749419
-553.9736342 / 0.194518
0.194296
0.194512
0.194409
0.194409
0.19438 / -553.8010402
-553.7942247
-553.7811777
-553.7805581
-553.7805329
-553.7792542
6H+ (O) / Eelectronic / Therm. Corr. / H298
ac-pro-oprot9
ac-pro-oprot8
ac-pro-oprot1
ac-pro-oprot6
ac-pro-oprot2
ac-pro-oprot11 / -554.3542058
-554.3511915
-554.351174
-554.3482927
-554.3469391
-554.34641 / 0.207397
0.207552
0.207583
0.207388
0.207532
0.207514 / -554.1468088
-554.1436395
-554.143591
-554.1409047
-554.1394071
-554.138896
6H+ (N) / Eelectronic / Therm. Corr. / H298
ac-pro-nprot5
ac-pro-nprot1
ac-pro-nprot33
ac-pro-nprot8
ac-pro-nprot2
ac-pro-nprot24
ac-pro-nprot34 / -554.3293438
-554.3281889
-554.3229303
-554.3229303
-554.3228854
-554.2395339
-554.2357181 / 0.207554
0.207651
0.207612
0.207613
0.207608
0.20703
0.20715 / -554.1217898
-554.1205379
-554.1153183
-554.1153173
-554.1152774
-554.0325039
-554.0285681
7 / Eelectronic / Therm. Corr. / H298
ac-pip37
ac-pip2
ac-pip6
ac-pip1
ac-pip16
ac-pip24
ac-pip14
ac-pip10
ac-pip36
ac-pip19
ac-pip35 / -593.162261
-593.161283
-593.161283
-593.160509
-593.160508
-593.158571
-593.158571
-593.158713
-593.158712
-593.158712
-593.156312 / 0.225198
0.224822
0.224823
0.224774
0.224778
0.224681
0.224682
0.224665
0.224664
0.224665
0.224644 / -593.0930345
-593.0929412
-593.0929402
-593.0920105
-593.0920064
-593.0904951
-593.0904949
-593.0904107
-593.0904097
-593.0904084
-593.088065
7H+ (O) / Eelectronic / Therm. Corr. / H298
ac-pip_oprot2
ac-pip_oprot1
ac-pip_oprot5
ac-pip_oprot25
ac-pip_oprot32
ac-pip_oprot9
ac-pip_oprot21
ac-pip_oprot40
ac-pip_oprot3
ac-pip_oprot6
ac-pip_oprot15 / -593.515104
-593.513780
-593.513444
-593.511899
-593.511899
-593.511324
-593.509318
-593.509317
-593.508552
-593.508126
-593.506290 / 0.238221
0.238113
0.237824
0.238145
0.238145
0.238092
0.237836
0.237836
0.237881
0.237874
0.237845 / -593.4383186
-593.4371477
-593.4364958
-593.4348848
-593.4348846
-593.434426
-593.4333653
-593.4333647
-593.4320119
-593.431932
-593.4302543
7H+ (N) / Eelectronic / Therm. Corr. / H298
ac_pip_nprot2
ac_pip_nprot14
ac_pip_nprot35
ac_pip_nprot1
ac_pip_nprot10 / -593.657977
-593.6549241
-593.6533871
-593.6513583
-593.6504717 / 0.23807
0.237883
0.237845
0.237834
0.23761 / -593.419907
-593.4170411
-593.4155421
-593.4135243
-593.4128617
8 / Eelectronic / Therm. Corr. / H298
ac-nma22
ac-nma1
ac-nma2
ac-nma16
ac-nma5
ac-nma4
ac-nma3
ac-nma30
ac-nma25 / -515.874719
-515.873749
-515.873694
-515.871765
-515.871214
-515.871014
-515.869772
-515.867621
-515.866380 / 0.187091
0.186616
0.186586
0.186462
0.186608
0.186757
0.186920
0.186616
0.186586 / -515.687628
-515.687133
-515.687108
-515.685303
-515.684606
-515.684257
-515.682852
-515.681005
-515.679794
8H+ (O) / Eelectronic / Therm. Corr. / H298
ac-nma-oprot-stump
ac-nma-oprot12
ac-nma-oprot2
ac-nma-oprot1
ac-nma-oprot6
ac-nma-oprot9
ac-nma-oprot24
ac-nma-oprot35
ac-nma-oprot36
ac-nma-oprot28
ac-nma-oprot34 / -516.229756
-516.229125
-516.227898
-516.227897
-516.227446
-516.226740
-516.225372
-516.224469
-516.223245
-516.214427
-516.212938 / 0.199830
0.200144
0.200058
0.200059
0.199957
0.200050
0.199830
0.199737
0.199892
0.199767
0.199652 / -516.029926
-516.028981
-516.027840
-516.027838
-516.027489
-516.026690
-516.025542
-516.024732
-516.023353
-516.014660
-516.013286
8H+ (N) / Eelectronic / Therm. Corr. / H298
ac-nma-nprot11
ac-nma-nprot1
ac-nma-nprot15
ac-nma-nprot3
ac-nma-nprot4
ac-nma-nprot10
ac-nma-nprot5
ac-nma-nprot9
ac-nma-nprot25
ac-nma-nprot8
ac-nma-nprot31
ac-nma-nprot13
ac-nma-nprot19
ac-nma-nprot22
ac-nma-nprot20
ac-nma-nprot30 / -516.215077
-516.212491
-516.212491
-516.212090
-516.212029
-516.207916
-516.207665
-516.207336
-516.206902
-516.206281
-516.205549
-516.205315
-516.204288
-516.202220
-516.200661
-516.193612 / 0.199959
0.199789
0.199790
0.199692
0.200002
0.199846
0.199864
0.199817
0.199586
0.199900
0.199735
0.199804
0.199766
0.199589
0.199636
0.199352 / -516.015118
-516.012702
-516.012701
-516.012398
-516.012027
-516.008070
-516.007801
-516.007519
-516.007316
-516.006381
-516.005814
-516.005511
-516.004522
-516.002631
-516.001025
-515.994260
9H (O1) / Eelectronic / Therm. Corr. / H298
hi_stump01 / -573.811403 / 0.249010 / -573.562393
hi_stump1 / -573.810621 / 0.249277 / -573.561344
hi_stump02 / -573.810616 / 0.249280 / -573.561336
hi_stump03 / -573.800585 / 0.249279 / -573.551306
nacpronme_hi05a.log: / -573.800952 / 0.250309 / -573.550643
nacpronme_hi02a.log: / -573.800609 / 0.250269 / -573.550340
nacpronme_hi07a.log: / -573.800603 / 0.250278 / -573.550325
hi_stump05 / -573.798960 / 0.249557 / -573.549403
nacpronme_hi04a.log: / -573.796252 / 0.250324 / -573.545928
nacpronme_hi09a.log: / -573.796059 / 0.250382 / -573.545677
nacpronme_hi08a.log: / -573.796004 / 0.250456 / -573.545548
nacpronme_hi03a.log: / -573.795224 / 0.250329 / -573.544895
9H (O2) / Eelectronic / Therm. Corr. / H298
nacpronme_hiii15 / -573.799020 / 0.249414 / -573.549606
nacpronme_hiii_2_19 / -573.797791 / 0.250029 / -573.547762
nacpronme_hiii_2_16 / -573.796962 / 0.249731 / -573.547231
nacpronme_hiii_2_10 / -573.792810 / 0.250030 / -573.542780
nacpronme_hiii_2_11 / -573.791209 / 0.250079 / -573.541130
nacpronme_hiii_2_07 / -573.790485 / 0.250119 / -573.540366
nacpronme_hiii_2_09 / -573.789861 / 0.249972 / -573.539889
nacpronme_hiii_2_12 / -573.788986 / 0.250077 / -573.538909
nacpronme_hiii_2_14 / -573.787566 / 0.250146 / -573.537420
nacpronme_hiii_2_13 / -573.783067 / 0.250005 / -573.533062
nacpronme_hiii_2_17 / -573.780598 / 0.250174 / -573.530424
10H (O1) / Eelectronic / Therm. Corr. / H298
nacpipnme_hi01a.log: / -613.133298 / 0.279400 / -612.853898
nacpipnme_hi04a.log: / -613.131835 / 0.279787 / -612.852048
nacpipnme_hi05a.log: / -613.131053 / 0.279739 / -612.851314
nacpipnme_hi06a.log: / -613.130093 / 0.279674 / -612.850419
nacpipnme_hi02a.log: / -613.128298 / 0.279355 / -612.848943
nacpipnme_hi07a.log: / -613.127338 / 0.279760 / -612.847578
nacpipnme_hi12a.log: / -613.124922 / 0.280823 / -612.844099
nacpipnme_hi20a.log: / -613.124505 / 0.280809 / -612.843696
nacpipnme_hi08a.log: / -613.122312 / 0.279572 / -612.842740
nacpipnme_hi19a.log: / -613.120900 / 0.280956 / -612.839944
nacpipnme_hi17a.log: / -613.119684 / 0.279873 / -612.839811
nacpipnme_hi32a.log: / -613.120842 / 0.281070 / -612.839772
nacpipnme_hi13a.log: / -613.119177 / 0.279698 / -612.839479
nacpipnme_hi16a.log: / -613.120197 / 0.280860 / -612.839337
nacpipnme_hi28a.log: / -613.120056 / 0.280937 / -612.839119
nacpipnme_hi37a.log: / -613.119092 / 0.281093 / -612.837999
nacpipnme_hi15a.log: / -613.117942 / 0.280966 / -612.836976
nacpipnme_hi14a.log: / -613.115809 / 0.279442 / -612.836367
nacpipnme_hi29a.log: / -613.117075 / 0.280914 / -612.836161
nacpipnme_hi25a.log: / -613.116100 / 0.281018 / -612.835082
nacpipnme_hi36a.log: / -613.115308 / 0.280631 / -612.834677
nacpipnme_hi38a.log: / -613.115109 / 0.280950 / -612.834159
nacpipnme_hi33a.log: / -613.114321 / 0.280787 / -612.833534
nacpipnme_hi44a.log: / -613.113962 / 0.281029 / -612.832933
nacpipnme_hi24a.log: / -613.112717 / 0.280964 / -612.831753
nacpipnme_hi59a.log: / -613.110925 / 0.280971 / -612.829954
nacpipnme_hi52a.log: / -613.110597 / 0.281045 / -612.829552
nacpipnme_hi56a.log: / -613.110596 / 0.281048 / -612.829548
nacpipnme_hi48a.log: / -613.110059 / 0.280782 / -612.829277
nacpipnme_hi50a.log: / -613.109753 / 0.280830 / -612.828923
nacpipnme_hi57a.log: / -613.109156 / 0.281009 / -612.828147
nacpipnme_hi27a.log: / -613.108816 / 0.280712 / -612.828104
nacpipnme_hi23a.log: / -613.102597 / 0.280554 / -612.822043
nacpipnme_hi55a.log: / -613.100671 / 0.280808 / -612.819863
nacpipnme_hi54a.log: / -613.098524 / 0.280358 / -612.818166
nacpipnme_hi46a.log: / -613.098518 / 0.280692 / -612.817826
10H (O2) / Eelectronic / Therm. Corr. / H298
nacpipnme_hiii_stump2 / -613.122102 / 0.280638 / -612.841464
nacpipnme_hiii12a.log: / -613.115808 / 0.279444 / -612.836364
nacpipnme_hiii13a.log: / -613.115849 / 0.280436 / -612.835413
II.Figures S1-S6:Low-energy Structures for neutral, protonated and deprotonated 5-10
Figure S1.Lowest energy structures for N-acetylAze, N-acetylAzeH+ (O-protonated) and N-acetylAzeH+ (N-protonated) obtained at the B3LYP/6-311++G**//B3LYP/6-31+G* level of theory.
Figure S2.Lowest energy structures for N-acetylPro, N-acetylProH+ (O-protonated) and N-acetylProH+ (N-protonated) obtained at the B3LYP/6-311++G**//B3LYP/6-31+G* level of theory.
Figure S3.Lowest energy structures for N-acetylPip, N-acetylPipH+ (O-protonated) and N-acetylPipH+ (N-protonated) obtained at the B3LYP/6-311++G**//B3LYP/6-31+G* level of theory.
Figure S4.Lowest energy structures for N-acetylNMeA, N-acetylNMeAH+ (O-protonated) and N-acetylNMAH+ (N-protonated) obtained at the B3LYP/6-311++G**//B3LYP/6-31+G* level of theory.
Figure S5.Lowest energy structures for N-acetylPro-NMeH+ (N terminal amide oxygen-protonated) and N-acetylProNMeH+ (C-terminal amide oxygen protonated)obtained at the B3LYP/6-311++G**//B3LYP/6-31+G* level of theory.
Figure S6.Lowest energy structures for N-acetylPip-NMeH+ (N terminal amide oxygen-protonated) and N-acetylPipNMeH+ (C-terminal amide oxygen protonated) obtained at the B3LYP/6-311++G**//B3LYP/6-31+G* level of theory.
III.Gaussian Archive files for structures shown in Figures S1-S6. Cartesian coordinates for other conformers are available upon request.
5
1\1\GINC-STIMPY\FOpt\RB3LYP\6-31+G(d)\C6H9N1O3\IONLAB\24-Sep-2009\0\\#
B3LYP/6-31+G* OPT GEOM=CHECK GUESS=READ\\1 23.259 -135.470\\0,1\C,1.8
696545894,0.650791028,0.3637528792\N,0.7322623053,-0.0951771901,-0.211
7919957\C,-0.0676239124,-0.0536262921,1.0312215132\C,-1.4760050142,0.5
517272765,0.9312148266\O,-1.8537667409,1.4109975116,1.6973859945\C,1.0
37601497,0.8281266086,1.6666186147\C,0.5314992089,-0.8425090201,-1.316
4492731\O,-2.2619154864,0.0338296562,-0.0167802888\H,-1.7653958217,-0.
6318601726,-0.5702320664\O,-0.5368713163,-1.4631787426,-1.4716199723\C
,1.6405533427,-0.8970947286,-2.3417489155\H,2.1102546692,1.570796686,-
0.1793371033\H,2.773850498,0.0408631671,0.4701983476\H,-0.1645618125,-
1.0550275758,1.4750171149\H,1.4931618921,0.4181053653,2.569315185\H,0.
7006012074,1.8480645286,1.856701154\H,2.1535877377,-1.8628619294,-2.25
87608033\H,2.3782022986,-0.0991438463,-2.219076917\H,1.2008132744,-0.8
403725279,-3.3408246793\\Version=x86-Linux-G98RevA.11.4\HF=-514.505912
8\RMSD=3.916e-09\RMSF=2.108e-06\Dipole=2.7044201,-0.3119531,-0.2508976
\PG=C01 [X(C6H9N1O3)]\\@
5H+ (O)
1\1\GINC-STIMPY\FOpt\RB3LYP\6-31+G(d)\C6H10N1O3(1+)\IONLAB\05-Nov-2009
\0\\# B3LYP/6-31+G* OPT GEOM=CHECK GUESS=READ\\1 127.987 40.558\\1,1\C
,1.8277340495,-0.652989301,0.6739381309\N,0.7819098747,0.2222575417,0.
0622977421\C,0.0248699221,-0.9423879164,-0.4864934338\C,-1.4764702886,
-0.9209143941,-0.260957637\O,-2.1341981295,0.1083687367,-0.3140994134\
C,0.954926973,-1.8868571676,0.3205894527\C,0.6500431702,1.5265715259,-
0.0126993237\O,-1.978545399,-2.1278378163,-0.0649180574\H,-2.955227500
5,-2.0805288126,0.003244582\O,-0.4072841863,2.087758276,-0.5239077048\
C,1.7047936552,2.4516520728,0.489753323\H,-1.1788968141,1.4465250789,-
0.6078396585\H,1.979914315,-0.4506396306,1.7361585822\H,2.7751339846,-
0.5866064335,0.132376433\H,0.1855752662,-1.0090743463,-1.5716735924\H,
1.4420942389,-2.6644137282,-0.2669172223\H,0.4645832321,-2.3339083167,
1.1865566498\H,1.9208438952,3.1880973273,-0.2920699291\H,2.6230386247,
1.9344616241,0.7696980907\H,1.3144084653,3.0035219582,1.3530002014\\Ve
rsion=x86-Linux-G98RevA.11.4\HF=-514.8605602\RMSD=9.550e-09\RMSF=2.051
e-05\Dipole=1.0877137,-0.4370493,0.2711123\PG=C01 [X(C6H10N1O3)]\\@
5H+ (N)
1\1\GINC-STIMPY\FOpt\RB3LYP\6-31+G(d)\C6H10N1O3(1+)\IONLAB\04-Dec-2009
\0\\# B3LYP/6-31+G* OPT GEOM=CHECK GUESS=READ\\1 23.259 -135.470\\1,1\
C,-1.0669735236,0.104140341,-1.632687471\N,-0.6963522006,0.1211991177,
-0.1298684975\C,0.7351045493,-0.2398721907,-0.4999672602\C,1.677835863
8,0.7179199493,0.2102492222\O,1.2598351429,1.6436170786,0.8765676944\C
,0.4273991647,0.0026074684,-2.0040918907\C,-1.4679922089,-0.8441232551
,0.8007255728\O,2.9486763205,0.4180092102,-0.0237116441\H,3.5353551915
,1.0630897644,0.4221997761\O,-1.1504033197,-1.9910209634,0.7539732035\
C,-2.5221869127,-0.1725946748,1.6172250993\H,-1.6160964014,1.001273337
6,-1.9195719893\H,-1.6487913041,-0.7947129868,-1.8412858066\H,0.928225
9063,-1.2838691582,-0.244317384\H,0.6961514473,-0.8208056644,-2.666072
2057\H,0.8455656296,0.9343859565,-2.3905372298\H,-2.0552337258,0.51260
65026,2.3380146107\H,-3.0948724185,-0.9289095182,2.1564338285\H,-3.192
8351939,0.4206673836,0.9828520449\H,-0.6869904721,1.0745721267,0.26801
0173\\Version=x86-Linux-G98RevA.11.4\HF=-514.8392527\RMSD=9.911e-09\RM
SF=3.287e-06\Dipole=-0.8764615,0.5855476,-0.7056253\PG=C01 [X(C6H10N1O
3)]\\@
6
1\1\GINC-REN\FOpt\RB3LYP\6-31+G(d)\C7H11N1O3\IONLAB\28-Jan-2010\0\\# O
PT RB3LYP/6-31+G(D) FREQ\\1 101.745 -53.398\\0,1\C,-0.5308380825,-0.40
79660915,-1.7953576663\N,-0.5324422432,-0.3510939545,-0.3186872158\C,0
.8383499796,-0.447888995,0.2438313282\C,1.3053645056,0.8887590613,0.87
81999347\O,2.2758122689,1.4993886942,0.4859617641\C,1.6862726078,-0.86
60397839,-0.9637959407\C,0.9508034277,-0.2374559288,-2.1588479014\C,-1
.6313788491,-0.3988138333,0.4741535767\O,0.5741215779,1.3099925363,1.9
161384765\H,-0.1986900287,0.6995587989,2.0641424391\O,-1.5323174022,-0
.341645396,1.7147353208\C,-2.9838367728,-0.5049701872,-0.1975609497\H,
-1.1665955459,0.3780252373,-2.2146157019\H,-0.9150866741,-1.3795351496
,-2.1362018719\H,0.8330665074,-1.2036100876,1.0389034691\H,2.715399402
2,-0.5161554171,-0.8667863111\H,1.6892053283,-1.9596831765,-1.04581651
98\H,1.2039431832,0.8256643131,-2.2321211263\H,1.1949135625,-0.7129931
377,-3.1134326038\H,-3.0187877105,-1.324326708,-0.9241340756\H,-3.7373
629743,-0.6679761573,0.5742273096\H,-3.2222618026,0.4230570402,-0.7317
732761\\Version=x86-Linux-G98RevA.11.4\HF=-553.8494611\RMSD=3.252e-09\
RMSF=1.184e-05\Dipole=-1.0879452,-1.4599027,-1.8706764\PG=C01 [X(C7H11
N1O3)]\\@
6H+ (O)
1\1\GINC-WILLOW\FOpt\RB3LYP\6-31+G(d)\C7H12N1O3(1+)\IONLAB\21-Jan-2010
\0\\# B3LYP/6-31+G* OPT GEOM=CHECK GUESS=READ\\1 351.587 267.744\\1,1\
C,1.0808347859,0.2118669519,1.6268187726\N,0.0217662244,-0.283099102,0
.6889277285\C,-0.5054113218,0.8370306252,-0.1631848115\C,-0.2384867392
,0.5629574191,-1.6501645921\O,-0.6285495669,-0.4676729659,-2.183691823
3\C,0.1471740045,2.0871108745,0.4500732985\C,1.4684940224,1.5688679458
,1.0359931503\C,-0.4733583168,-1.5064609672,0.7353029212\O,0.388954325
9,1.5326663534,-2.2934289483\H,0.4716217739,1.3008806038,-3.24224306\O
,-1.3115428497,-1.952208711,-0.1555339518\C,-0.1046767264,-2.474108724
7,1.8107954974\H,-1.2736279306,-1.4312312052,-1.0192875197\H,1.9020351
27,-0.5063471819,1.6657118963\H,0.6457832796,0.3170508875,2.626951945\
H,-1.5981937959,0.8524854834,-0.063634893\H,0.2801352531,2.8781018553,
-0.2891110922\H,-0.5019444444,2.4710165404,1.2441695724\H,2.2216347437
,1.4446249037,0.2498903464\H,1.8826525447,2.2348932172,1.7966108325\H,
-0.884059717,-3.2363803323,1.8748444738\H,0.832930456,-2.9785472527,1.
5405281558\H,0.0303556126,-1.9907159629,2.7805076123\\Version=x86-Linu
x-G98RevA.11.4\HF=-554.2032444\RMSD=8.665e-09\RMSF=2.804e-05\Dipole=0.
4877162,0.2494823,0.8492044\PG=C01 [X(C7H12N1O3)]\\@
6H+ (N)
1\1\GINC-STIMPY\FOpt\RB3LYP\6-31+G(d)\C7H12N1O3(1+)\IONLAB\22-Jan-2010
\0\\# B3LYP/6-31+G* OPT GEOM=CHECK GUESS=READ\\1 129.356 104.713\\1,1\
C,-1.7365637064,0.5058916644,-0.6067124883\N,-0.2828756688,0.028410448
4,-0.6587314451\C,0.2999078823,0.1533832946,0.7512396297\C,0.702417575
7,-1.2680344912,1.1641158642\O,0.4342578497,-2.2423115979,0.4929916077
\C,-0.8404039712,0.7535740096,1.6073093113\C,-2.1201826694,0.340997253
6,0.8632272488\H,-0.266708214,-0.9910801473,-0.8593344121\O,1.34813268
96,-1.2658974766,2.3253962796\H,1.5895620701,-2.1817027095,2.573998455
3\C,0.5754998288,0.6509796915,-1.7875372415\O,1.0065787974,-0.11683301
64,-2.5895291565\C,0.744153416,2.1409077255,-1.7532154618\H,-2.3149661
761,-0.0873174766,-1.3172510172\H,-1.7514125269,1.5546629414,-0.912213
5025\H,1.1922178577,0.7839779925,0.7292161761\H,-0.7970588639,0.390790
9896,2.6368280618\H,-0.7405818709,1.8437842915,1.6373401899\H,-2.38808
06116,-0.6993710233,1.0778862159\H,-2.9772433428,0.9680732345,1.122631
8892\H,0.5183933869,2.5908067474,-0.784060614\H,1.7712449871,2.3767097
114,-2.0463899874\H,0.0840381581,2.5859341494,-2.5089623601\\Version=x
86-Linux-G98RevA.11.4\HF=-554.179992\RMSD=9.365e-09\RMSF=6.106e-06\Dip
ole=-0.7159297,1.4649031,0.5282306\PG=C01 [X(C7H12N1O3)]\\@
7
N-N= 7.722786653019D+02 E-N=-2.926356425972D+03 KE= 5.876025942403D+02
1\1\GINC-REN\FOpt\RB3LYP\6-31+G(d)\C8H13N1O3\IONLAB\15-Oct-2009\0\\# B
3LYP/6-31+G* OPT GEOM=CHECK GUESS=READ\\1 283.335 121.778\\0,1\N,0.495
3191923,-0.0846938043,-0.5167104358\C,-1.3929683384,-0.5425498343,1.04
54759473\C,0.1260323063,-0.2754265599,0.9069318555\C,0.2570412654,1.24
92493758,-1.0995660816\C,0.8428315305,2.3679126839,-0.2350510702\C,0.3
172642994,2.2721060637,1.2011327164\C,0.6246506617,0.8859749905,1.7792
088037\O,-2.1606924043,0.1960359475,1.6210381084\O,-1.8096713417,-1.68
56202941,0.4724758702\H,-1.0414720541,-2.1604718037,0.0646277255\C,0.7
179927723,-1.200867617,-1.2739837911\O,0.5304197879,-2.3382136293,-0.8
060855468\C,1.2081654735,-1.0417811673,-2.7001995514\H,0.6324294544,-1
.1933291855,1.2213722467\H,0.688690081,1.2733369471,-2.1004360978\H,-0
.8288720736,1.3972421379,-1.2065084418\H,0.5771474705,3.3313390191,-0.
6878524319\H,1.9398252033,2.296405343,-0.2424777711\H,0.7789118459,3.0
437105517,1.8290966287\H,-0.7650985948,2.4463946021,1.2178757345\H,1.7
118377367,0.7728961151,1.8891594004\H,0.1824526133,0.7769381701,2.7745
181323\H,0.3963471578,-0.7064795487,-3.3570422612\H,1.5408892214,-2.02
30349093,-3.0422493494\H,2.0331694337,-0.3274146152,-2.7862308902\\Ver
sion=x86-Linux-G98RevA.11.4\HF=-593.1622606\RMSD=6.739e-09\RMSF=3.639e
-05\Dipole=1.7080738,1.1790914,-1.0748773\PG=C01 [X(C8H13N1O3)]\\@
7H+ (O)
1\1\GINC-REN\FOpt\RB3LYP\6-31+G(d)\C8H14N1O3(1+)\IONLAB\06-Nov-2009\0\
\# B3LYP/6-31+G* OPT GEOM=CHECK GUESS=READ\\1 267.761 177.504\\1,1\N,-
0.2346373218,0.6138225264,0.324588235\C,-0.2549726417,-1.7202382988,-0
.3968167574\C,-0.1695889243,-0.2614842823,-0.8806519298\C,1.0225795527
,0.7343105169,1.1233821631\C,2.2190962736,1.0876916746,0.2370072257\C,
2.3625741486,0.1016362629,-0.9268091827\C,1.0664196251,0.0671894369,-1
.7418522769\O,-0.4486485501,-2.0477284817,0.7521213009\O,-0.1232705143
,-2.5658960602,-1.4265813195\H,-0.2212341539,-3.4825927942,-1.09993802
12\C,-1.3770408665,1.0844662856,0.746842851\O,-2.4365623555,0.81335704
34,0.0014837092\C,-1.543261706,1.8865135789,2.002670634\H,-3.253109375
2,1.2028118222,0.3594881979\H,-1.0666951784,-0.0810889119,-1.475533639
8\H,0.8731997561,1.4873869944,1.8952919531\H,1.164318635,-0.2355401767
,1.6128114348\H,3.1108852479,1.0811418805,0.8734302192\H,2.1059821305,
2.1104675822,-0.1462102501\H,3.194620001,0.3983391098,-1.5734024285\H,
2.6029961543,-0.9003988725,-0.5450506337\H,0.8960855147,1.0437833014,-
2.2120680626\H,1.1137063135,-0.6719901679,-2.5460745425\H,-1.268418061
6,1.2855766539,2.876618237\H,-2.5821109836,2.2044688761,2.1214062657\H
,-0.9147461579,2.7825059564,1.9882877378\\Version=x86-Linux-G98RevA.11
.4\HF=-593.5151039\RMSD=7.997e-09\RMSF=5.651e-06\Dipole=-1.01671,1.630
6301,0.6763897\PG=C01 [X(C8H14N1O3)]\\@
7H+ (N)
1\1\GINC-REN\FOpt\RB3LYP\6-31+G(d)\C8H14N1O3(1+)\IONLAB\09-Dec-2009\0\
\# B3LYP/6-31+G* OPT GEOM=CHECK GUESS=READ\\1 283.335 121.778\\1,1\N,0
.225823838,-0.1680943235,-0.8970924346\C,-0.2036656059,-0.3847268646,1
.5198112823\C,0.8946813786,-0.1754947653,0.4765484641\C,-0.555719828,1
.1053557857,-1.1844008121\C,0.3360930882,2.3351455012,-1.0033025975\C,
0.973031275,2.3755890994,0.3920717628\C,1.7562389404,1.084620628,0.661
8096818\O,-1.353603958,-0.6480119148,1.233478266\O,0.2783433578,-0.281
2014241,2.756616782\H,-0.4313544764,-0.4774345966,3.4015328024\C,-0.50
54817866,-1.5736702419,-1.1626734246\O,0.1607486938,-2.5171974402,-0.8
854615061\C,-1.8513980637,-1.5164092044,-1.8017532246\H,1.5243626227,-
1.0707143687,0.495294037\H,-0.9254383002,1.0246525386,-2.2087199005\H,
-1.404153549,1.112473331,-0.499398902\H,-0.2849319828,3.220235524,-1.1
79758157\H,1.1170933099,2.3454318,-1.7773640875\H,1.6466725027,3.23439
43765,0.4720739283\H,0.1961723814,2.5157470171,1.1560855713\H,2.617091
3486,1.0158418297,-0.0170013399\H,2.1591828989,1.0626243851,1.67846353
97\H,-2.5316670394,-0.8748079645,-1.2372008832\H,-2.2433699277,-2.5347
046249,-1.8357338751\H,-1.7730640339,-1.1336187718,-2.8271570298\H,1.0
060562422,-0.1946336063,-1.5672037905\\Version=x86-Linux-G98RevA.11.4\
HF=-593.4986931\RMSD=8.240e-09\RMSF=6.074e-06\Dipole=0.0873416,0.86968
28,-1.0113871\PG=C01 [X(C8H14N1O3)]\\@
8
1\1\GINC-WILLOW\FOpt\RB3LYP\6-31+G(d)\C6H11N1O3\IONLAB\02-Feb-2010\0\\
# B3LYP/6-31+G* OPT GEOM=CHECK GUESS=READ\\1 199.134 42.489\\0,1\C,-1.
8339241707,1.9346787497,-1.3434068283\C,-0.7968485092,0.848460812,-1.1
324586998\O,0.0372275757,0.6039334416,-2.0229166576\N,-0.7953264485,0.
1452831671,0.0377410458\C,0.1260457055,-1.0135300571,0.1473941981\C,1.
5348614909,-0.5272034628,0.5673630692\O,2.0332196775,-0.7754098647,1.6
425837344\O,2.1720439384,0.2093510984,-0.3581987128\H,1.5869082985,0.3
359451849,-1.1484571295\C,-1.5111853449,0.570046459,1.2418518086\C,-0.
4010640948,-2.1067445569,1.0729016889\H,-1.5553878389,2.8476395438,-0.
8024341022\H,-2.8358097068,1.6364974017,-1.0193256281\H,-1.8497713714,
2.1668120798,-2.4095400073\H,0.2081755962,-1.4148500222,-0.8676195516\
H,-1.9635908596,1.5477028743,1.08433498\H,-2.2983644769,-0.1416751647,
1.5126216658\H,-0.8101363712,0.6547308366,2.0794740381\H,-0.4295219131
,-1.7915774195,2.1187548127\H,-1.4007364183,-2.4253768968,0.7580958394
\H,0.2682802072,-2.970075654,1.0162894307\\Version=x86-Linux-G98RevA.1
1.4\HF=-515.7348141\RMSD=4.650e-09\RMSF=2.043e-05\Dipole=-2.3495191,0.
2301114,0.0761439\PG=C01 [X(C6H11N1O3)]\\@
8H+ (O)
1\1\GINC-STIMPY\FOpt\RB3LYP\6-31+G(d)\C6H12N1O3(1+)\IONLAB\16-Feb-2010
\0\\# B3LYP/6-31+G* OPT GEOM=CHECK GUESS=READ\\12 190.533 105.188\\1,1
\C,-2.9461303031,-0.2673639509,0.6373776742\C,-1.5952402937,0.21833764
9,0.222593098\O,-1.4858796462,1.5125855674,0.1221223116\N,-0.577310203
3,-0.5882861695,-0.0459200855\C,0.6208656123,-0.079038421,-0.805095757
2\C,1.4977630692,0.753002892,0.1447988798\O,1.0619529026,1.7748272593,
0.6607151336\O,2.7211356469,0.2899675258,0.331158906\H,3.219619684,0.8
929965462,0.9218400184\C,-0.618804307,-2.0205764393,0.3259442943\C,1.3
512755954,-1.1676938454,-1.5872708146\H,-0.5350195057,1.836797689,0.22
90398545\H,-3.2330988466,-1.1954088042,0.1392534129\H,-3.6701503603,0.
5182143464,0.4094080282\H,-2.9677563515,-0.4257200127,1.7239557313\H,0
.2201606322,0.6458993458,-1.5238287904\H,-1.3865489114,-2.1827460854,1
.0793839431\H,-0.8203179201,-2.6444634451,-0.5480022141\H,0.3434345397
,-2.2986898312,0.7591458138\H,1.8374710966,-1.9063633336,-0.9476455921
\H,0.6666198508,-1.6712961721,-2.2752569837\H,2.1307100501,-0.69026718
31,-2.18790768\\Version=x86-Linux-G98RevA.11.4\HF=-516.0848112\RMSD=6.
297e-09\RMSF=8.712e-06\Dipole=-0.317935,-1.1565442,-0.011322\PG=C01 [X
(C6H12N1O3)]\\@
8H+ (N)
1\1\GINC-REN\FOpt\RB3LYP\6-31+G(d)\C6H12N1O3(1+)\IONLAB\07-Feb-2010\0\
\# B3LYP/6-31+G* OPT GEOM=CHECK GUESS=READ\\1 199.134 42.489\\1,1\C,-2
.6262893325,-0.798081727,-0.1333896129\C,-1.3459391013,-0.665787916,0.
6213811343\O,-0.8443395164,-1.385574221,1.421161901\N,-0.557217341,0.6
802430412,0.3118819714\C,0.9388573099,0.4198344619,0.212872214\C,1.109
9257528,-0.4953145554,-1.002256445\O,0.1994580338,-0.732840121,-1.7716
481132\O,2.3505166663,-0.9588044122,-1.0966013864\H,2.4326769607,-1.53
174156,-1.8860895402\C,-0.9375305342,1.6991184268,1.3560783239\C,1.764
1087666,1.70477991,0.0822151038\H,-3.2142959515,0.1263284882,-0.108072
0644\H,-3.2055291419,-1.617553017,0.2960804842\H,-2.3936139919,-1.0250
671044,-1.1815431611\H,1.2122581312,-0.1284065452,1.1185415194\H,-2.02
63721045,1.7471076044,1.4167592178\H,-0.5250689932,1.3822079746,2.3148
707283\H,-0.5463725969,2.6748786111,1.0701416752\H,1.4404062893,2.3161
57394,-0.7678085444\H,1.7280766243,2.3032414164,0.9954062116\H,2.80758
55046,1.4237418207,-0.0832258902\H,-0.873107981,0.9978620601,-0.612937
9551\\Version=x86-Linux-G98RevA.11.4\HF=-516.0716506\RMSD=5.326e-09\RM
SF=3.822e-05\Dipole=-0.6530942,1.4476805,0.1340243\PG=C01 [X(C6H12N1O3
)]\\@
9
1\1\GINC-WILLOW\FOpt\RB3LYP\6-31+G(d)\C8H14N2O2\IONLAB\12-Nov-2013\0\\
# OPT RB3LYP/6-31+G* GEOM=CHECK GUESS=READ\\conformation 01 from nacpr
onme\\0,1\C,0.6908061809,1.2529071614,-1.6707317414\N,0.1658158218,0.0
470296358,-0.9984893826\C,0.9351839287,-0.2891334842,0.224682492\C,0.1
375486847,0.0330904586,1.5178995706\O,0.4608787324,0.9496029316,2.2756
856153\C,2.1975184857,0.5717406877,0.0899154463\C,1.7073212067,1.81729
59733,-0.6670838521\C,-0.7513456761,-0.810352695,-1.5218600724\N,-0.91
4820484,-0.7869802255,1.7443511018\C,-1.8022867067,-0.5959676491,2.880
8817638\O,-1.0909840129,-1.845290496,-0.9271989721\C,-1.3548829535,-0.
4417846189,-2.8651154053\H,-0.1158689052,1.9579300895,-1.8978796076\H,
1.1775933092,0.9761930594,-2.6164690788\H,1.149028199,-1.3632436707,0.
2094924446\H,2.6230126921,0.8143722022,1.0653376549\H,2.9464811355,0.0
301613041,-0.5011087473\H,1.2140801326,2.4993053027,0.0327656956\H,2.5
133559066,2.3626698538,-1.1679403427\H,-1.1582568492,-1.447363308,1.00
7132595\H,-1.2208370489,-0.5251607038,3.8047828889\H,-2.394582191,0.32
26082829,2.7822022553\H,-2.4775433646,-1.4527042322,2.9434888598\H,-0.
5844081622,-0.3294399708,-3.6371799078\H,-2.0452898281,-1.2337905216,-
3.1587062288\H,-1.9020690487,0.5068419539,-2.8063728695\\Version=x86-L
inux-G98RevA.11.4\HF=-573.2945888\RMSD=2.429e-09\RMSF=3.142e-06\Dipole
=0.085455,0.3484203,-1.2587277\PG=C01 [X(C8H14N2O2)]\\@
9H+ (O1)
1\1\GINC-XANDER\Freq\RB3LYP\6-31+G(d)\C8H15N2O2(1+)\IONLAB\22-Nov-2013
\0\\# FREQ RB3LYP/6-31+G* GEOM=CHECK GUESS=READ\\conformation 01 from
nacpronme_hi_stump\\1,1\C,-1.110534126,-2.0390556085,-0.070661689\N,-0
.874792362,-0.6052163274,0.2737166559\C,0.6048961169,-0.334475746,0.40
73785123\C,1.0885448119,0.9367640211,-0.3132746152\O,0.4678943262,2.01
3609235,-0.1648082209\C,1.251881753,-1.6674424483,-0.0153129967\C,0.19
52730852,-2.7230180617,0.3313215115\C,-1.8505758431,0.2118413739,0.660
2970444\N,2.2194005042,0.8893702292,-1.0139041043\C,2.8048410511,2.089
2240372,-1.6285332712\O,-1.6383353784,1.4446968803,0.962149556\C,-3.27
03146679,-0.2580980366,0.7733404155\H,2.7143503269,0.0131381021,-1.106
3236615\H,-0.7127208449,1.8027779783,0.5821675822\H,-1.298506531,-2.11
66948963,-1.1478470711\H,-1.9784919316,-2.4217208983,0.4655862225\H,0.
7938275701,-0.149587741,1.4747533064\H,1.4297616112,-1.6811384666,-1.0
97717231\H,2.2034659127,-1.8316847491,0.4978796226\H,0.3476089833,-3.6
629431552,-0.204616591\H,0.1982913806,-2.9393878108,1.4054732105\H,3.0
15306242,2.8393906653,-0.8619796982\H,3.7309521083,1.799575754,-2.1256
245923\H,2.1114125521,2.5134158215,-2.3588447608\H,-3.6160265921,-0.69
98572548,-0.1671158631\H,-3.3734848204,-1.0138062168,1.5607118112\H,-3
.898547631,0.5985594449,1.0187497029\\Version=x86-Linux-G98RevA.11.4\H
F=-573.6598478\RMSD=3.888e-09\RMSF=2.233e-06\Dipole=0.4237654,-1.63997
44,-0.2937504\PG=C01 [X(C8H15N2O2)]\ \@
9H+ (O2)
1\1\GINC-XANDER\FOpt\RB3LYP\6-31+G(d)\C8H15N2O2(1+)\IONLAB\02-Dec-2013
\0\\# OPT RB3LYP/6-31+G* GEOM=CHECK GUESS=READ\\conformation 19 from n
acpronme_hiii_try2\\1,1\C,-1.8930033517,1.1792633408,0.42189928\N,-1.0
321442561,0.0139427232,0.1034602649\C,-0.017531806,0.3307860101,-0.920
0826007\C,1.4046002307,0.2178744237,-0.3473982645\O,2.2234689461,1.244
7162394,-0.2360609484\C,-0.4304191876,1.7359360344,-1.4016981192\C,-1.
1298511114,2.3638167274,-0.182864328\C,-1.3038030997,-1.2938145625,0.4
165742593\N,1.8524480908,-0.9361505368,0.0374209243\C,3.1911323562,-1.
1860400657,0.5933689027\O,-0.5380552647,-2.1945303957,0.0390979591\C,-
2.5365469582,-1.5804438193,1.2361767423\H,1.1428886384,-1.6951287261,-
0.0088593909\H,1.8385985625,2.0669476631,-0.5880507118\H,-2.0332600686
,1.2707992389,1.5017520904\H,-2.876615333,1.0603475044,-0.0490126777\H
,-0.0707508483,-0.4118441503,-1.7251147483\H,0.387944095,2.3368598978,
-1.8174462143\H,-1.1423158122,1.6101967181,-2.2239745442\H,-0.40361348
72,2.7550755355,0.540719614\H,-1.7943363095,3.186035883,-0.4590663135\
H,3.9524978659,-0.7561855034,-0.0609125812\H,3.2743059183,-0.740548428
6,1.5888016015\H,3.3259635475,-2.2651078711,0.661046507\H,-3.441621484
4,-1.2100276327,0.7412198611\H,-2.6165381107,-2.6592646907,1.373339586
8\H,-2.4760459015,-1.0984560254,2.2192382797\\Version=x86-Linux-G98Rev
A.11.4\HF=-573.6464011\RMSD=9.795e-09\RMSF=1.819e-06\Dipole=0.6113495,
1.2981348,-0.1318945\PG=C01 [X(C8H15N2O2)]\\@
10
1\1\GINC-WILLOW\Freq\RB3LYP\6-31+G(d)\C9H16N2O2\IONLAB\13-Dec-2013\0\\
# FREQ RB3LYP/6-31+G* GEOM=CHECK GUESS=READ\\conformation 01 from nacp
ipnme\\0,1\C,-1.5602437775,0.1292946061,-1.0418863568\N,-0.7352812154,
0.5932217079,0.0857429237\C,0.0157342551,-0.4450414012,0.8290107739\C,
1.2905798578,-0.8573293838,0.049541144\O,1.409216834,-1.9431469207,-0.
5204327951\C,-0.8876118356,-1.6363024976,1.1868277049\C,-0.41721931,1.
9061012805,0.3102351317\N,2.265490222,0.0867404042,0.0566568739\C,3.51
78665519,-0.0961371538,-0.6606504381\O,0.4939503944,2.2275747966,1.087
2883637\C,-1.2134698864,2.9843113976,-0.4089972224\H,2.0616382411,0.97
22596761,0.5138462073\C,-2.5134877044,-0.9926749548,-0.6208463933\C,-1
.7363803573,-2.1497858286,0.016600924\H,-0.8963963355,-0.2344963683,-1
.8414341729\H,-2.118520428,0.9756720598,-1.4417110178\H,0.3430413191,0
.0380977913,1.75273716\H,-0.2561389641,-2.4392651408,1.5813590052\H,-1
.5511093457,-1.3122324821,2.0006980498\H,3.360504482,-0.117536635,-1.7
460815086\H,3.9882471592,-1.0403407635,-0.3692776875\H,4.1859934238,0.
7317243536,-0.4117666616\H,-0.9805258081,3.0031432098,-1.4806432708\H,
-0.9244144675,3.9433948742,0.0235128097\H,-2.2953797672,2.8521557216,-
0.3007197633\H,-3.2500700828,-0.5916252624,0.0903570954\H,-3.066897889
6,-1.3328999286,-1.5054891099\H,-1.0826163461,-2.6152165925,-0.7295850
853\H,-2.428762825,-2.922608691,0.3735432112\\Version=x86-Linux-G98Rev
A.11.4\HF=-612.6080838\RMSD=3.324e-09\RMSF=6.547e-06\Dipole=-0.8788302
,0.5974475,-0.4717477\PG=C01 [X(C9H16N2O2)]\\@
6H+ (O1)
1\1\GINC-XANDER\SP\RB3LYP\6-311++G(d,p)\C9H17N2O2(1+)\IONLAB\08-Jan-20
14\0\\# RB3LYP/6-311++G** GEOM=CHECK GUESS=READ\\conformation 02 from
nacpipnme_hi\\1,1\C,1.5519292087,1.1312048832,0.9690962522\N,0.8684526
417,-0.1019322334,0.473138629\C,-0.5403727306,0.2524951186,0.091073314
9\C,-1.5661956936,-0.8672933184,-0.111359949\O,-1.294938703,-1.9584881
493,-0.6615011982\C,-0.4831699241,1.1898302571,-1.1453586522\C,1.59023
59719,-1.1697768003,0.1210136324\N,-2.8286047129,-0.6052383552,0.24637
73886\C,-3.3830375227,0.5739909254,0.9191300032\O,1.1143488813,-2.1887
877535,-0.4961035173\C,3.0562735958,-1.2720495082,0.4455375406\H,-3.47
0982962,-1.3592134541,0.018630711\C,1.6743906945,2.1470492974,-0.17515
92847\C,0.3070834942,2.4643256257,-0.8010563634\H,0.0606755323,-2.1542
780139,-0.6708883017\H,2.522361245,0.8690316787,1.3840633383\H,0.94640
44476,1.5258550823,1.7919798487\H,-0.8888012413,0.8416171319,0.9435742
861\H,-0.0224423367,0.6435352282,-1.9778032326\H,-1.501542065,1.445509
5078,-1.4584692231\H,-2.9675363564,0.6927953132,1.9250696821\H,-4.4592
217041,0.424183184,1.0132425763\H,-3.2184446456,1.4855104273,0.3374318
721\H,3.4054321227,-2.2452096736,0.0994221291\H,3.2319842028,-1.195906
9641,1.5236761534\H,3.6364245681,-0.4897747871,-0.0545062953\H,2.13917
30717,3.0607095685,0.212454904\H,2.3544585624,1.7434876998,-0.93731951
95\H,-0.2828745208,3.0714627651,-0.1001653517\H,0.437892586,3.07042776
5,-1.7036669395\\Version=x86-Linux-G98RevA.11.4\HF=-613.1282979\RMSD=2
.426e-05\Dipole=-0.2339793,1.2312501,0.9154384\PG=C01 [X(C9H17N2O2)]\\
@
6H+ (O2)
N-N= 8.918740128753D+02 E-N=-3.196617843253D+03 KE= 6.103929459946D+02
1\1\GINC-XANDER\SP\RB3LYP\6-311++G(d,p)\C9H17N2O2(1+)\IONLAB\08-Jan-20
14\0\\# RB3LYP/6-311++G** GEOM=CHECK GUESS=READ\\conformation 05 from
nacpipnme_hi\\1,1\C,1.3764603668,1.0167193658,-0.983872255\N,1.0599213
89,-0.0075406457,0.0398226674\C,-0.1835370144,0.1393798697,0.832697807
\C,-1.3390456647,-0.6126706759,0.1612050155\O,-1.2129489425,-1.8886008
133,0.0051996192\C,-0.4425222559,1.6052733909,1.2331294331\C,1.7382238
961,-1.1923487129,0.1403331213\N,-2.4499270539,-0.0317127733,-0.225938
8263\C,-3.6100248633,-0.7130527256,-0.825026174\O,1.1898077412,-2.1808
567362,0.6785036495\C,3.1445925025,-1.3110511852,-0.3860744445\H,-2.52
45481801,0.9684608409,-0.0781280351\C,1.1911203723,2.4423857146,-0.466
613558\C,-0.2150219903,2.6280112731,0.1109329488\H,-0.2686906356,-2.18
08102762,0.3508485284\H,0.7268681313,0.84729684,-1.8558638013\H,2.4024
117095,0.8560639254,-1.3137840949\H,-0.0176972199,-0.4303611274,1.7553
378708\H,-1.4416742658,1.6878135834,1.6790599635\H,0.2559702509,1.8281
897476,2.0479539136\H,-3.3735240711,-1.7664493061,-0.9634731188\H,-3.8
344930687,-0.2519403834,-1.7899741086\H,-4.4706054304,-0.6106115939,-0
.1586608186\H,3.5873603783,-2.2033503126,0.0597077914\H,3.7604837662,-
0.4381584258,-0.1527428996\H,3.1362124964,-1.4489994936,-1.4745338004\
H,1.9425756849,2.6589699278,0.3036636871\H,1.3680554839,3.1365022161,-
1.295370177\H,-0.338395769,3.6382838738,0.5145709946\H,-0.9566120911,2
.5236564059,-0.6956962969\\Version=x86-Linux-G98RevA.11.4\HF=-613.1310
529\RMSD=5.722e-05\Dipole=-1.0890714,1.2337685,-0.5038663\PG=C01 [X(C9
H17N2O2)]\\@
IV.Figures S7 and S8: Product ion fragmentation spectra for AAAXA (X=Aze, Pip) and AGXGA (X= Aze, Pro, Pip, NMeA)
Figure S7.Product ion fragmentation spectrum for a) AAA(Aze)A and b) AAA(Pip)A
Figure S8.Product ion fragmentation spectrum for a) AG(Aze)GA, b) AGPGA, c) AGPipGA, and d) AG(NMeA)GA