The Influence of Secondary Interactions on Complex Stability and Double Proton Transfer

The influence of secondary interactions on complex stability and double proton transfer reaction in 2-[1H]-pyridone/2-hydroxypyridine dimers

Borys Osmialowski* and Robert Dobosz

Faculty of Chemical Technology and Engineering, University of Technology and Life Sciences, Seminaryjna 3, PL-85-326 Bydgoszcz, Poland

(B. O.: Fax: +48 52 3749005; E-mail: )

Supplementary Material

The basis set study for 2-pyridone dimer (geometry parameters)S2

Cartesian coordinates of optimized structuresS3

BSSE energyS11

The basis set study for 2-pyridone dimer

The hydrogen bond length and N1…O3’ are less sensitive to addition of another functions to the basis set when triple- basis is used. The N1-N1’ and O3-O3’ distances behave in various way due to shift of one molecule with respect to counterpart.

M05/6-311+G(2d,p) optimized structures

2-[1H]-pyridone

N 1.7485089932 -0.3999005467 -0.0000532802

C 1.7303800705 1.0051736948 -0.0002955616

C 3.0553092793 1.585608909 -0.0000332154

C 4.1719454508 0.8121900513 -0.0000202915

C 4.0944962033 -0.6065483377 -0.000043087

C 2.8627906056 -1.1738755185 0.000006968

O 0.6692744395 1.6015796134 0.0001708742

H 0.8346809294 -0.8268246459 0.0000319529

H 3.1047783228 2.6669790996 0.0000855098

H 5.1487430524 1.2859228745 0.0000534378

H 4.9810155263 -1.22482306 0.0000009751

H 2.7032421387 -2.2454399296 0.0000956946

6-amino-2-[1H]-pyridone

N 1.6434221111 -0.249929442 -0.0683059878

C 1.6516130718 1.1659272536 -0.0508289443

C 2.9750306201 1.7219955864 0.0021629349

C 4.0702269506 0.9105394015 0.0270920205

C 3.9791718066 -0.4973872566 0.0140143759

C 2.7304717422 -1.0620530888 -0.0400227604

O 0.5880659953 1.7582108315 -0.085341193

H 0.7197522049 -0.6458852919 -0.16154631

H 3.0533834888 2.8005758459 0.0144265444

H 5.0579045809 1.3594210394 0.0659115097

H 4.8596670892 -1.1249173829 0.0455831692

N 2.4912084299 -2.4171105593 -0.1276063344

H 1.6499678814 -2.7484927736 0.3177645859

H 3.286165182 -2.993203411 0.0935210606

6-hydroxy-2-[1H]-pyridone

N 1.5936661998 -0.2430897653 0.0009076338

C 1.6293561788 1.1790659296 0.0037744357

C 2.9666229904 1.7023217338 0.0005831002

C 4.0449555712 0.8685671673 0.0002599201

C 3.9300129676 -0.5387315004 0.0006451778

C 2.6716907706 -1.0643460983 0.0002538985

O 0.5763622827 1.7873138596 -0.0028112229

H 0.6550622154 -0.6157274232 0.0002980628

H 3.0694537364 2.7788517537 -0.0009883057

H 5.0414485438 1.2981933986 -0.0011129098

H 4.7845302659 -1.1989926626 0.0000187363

O 2.4776802525 -2.3919242459 -0.0008139213

H 1.5450231728 -2.6197151634 -0.0010126999

2-amino-6-hydroxypyridine

C -4.0452202167 0.1199519646 0.1147594321

C -2.8616160027 -0.626474347 0.1014183762

N -1.6566254031 -0.0535457865 0.0492526118

C -1.5905719732 1.2674105423 0.0190404083

C -2.6963735063 2.111506363 0.0287972017

C -3.9378835801 1.4992635736 0.0761800726

O -0.361366403 1.8138979358 -0.029130466

N -2.8767301921 -1.9996269914 0.1872536796

H -5.0094682387 -0.3720562746 0.1625001841

H -2.5698909509 3.1849905731 -0.0006328899

H -4.8363265501 2.1072253068 0.0846791611

H 0.2648369945 1.081406208 -0.0234569954

H -2.0184367649 -2.4484295455 -0.0854708508

H -3.712337373 -2.4682483149 -0.1157204907

2,6-dihydroxypyridine

C -4.0691191529 0.0330296519 0.0000057988

C -2.8696764564 -0.6695502681 0.000012677

N -1.6753714394 -0.0934134112 0.0000062664

C -1.6260726392 1.2316955933 -0.0000075274

C -2.7503985573 2.0490896268 -0.0000155926

C -3.9827292241 1.4158349162 -0.0000085393

O -0.4079974266 1.8012917919 -0.0000140851

O -2.9034802214 -2.0138015966 0.0000270916

H -5.0123496206 -0.4958128373 0.0000116104

H -2.643848707 3.1251964227 -0.0000265405

H -4.8903348025 2.0095147639 -0.0000142482

H 0.2376864596 1.0864615413 -0.0000070143

H -1.9898252728 -2.3189655198 0.0000301031

1+1

N 1.17676 1.40173 0.

C 2.0308 0.30816 0.

C 3.42841 0.6499 0.

C 3.83649 1.9482 0.

C 2.90299 3.01173 0.

C 1.58239 2.68963 0.

O 1.58239 -0.83999 0.

H 0.16684 1.19641 0.

H 4.12829 -0.17569 0.

H 4.89825 2.17462 0.

H 3.2169 4.04598 0.

H 0.79023 3.42886 0.

N -1.17676 -1.40173 0.

C -2.0308 -0.30816 0.

C -3.42841 -0.6499 0.

C -3.83649 -1.9482 0.

C -2.90299 -3.01173 0.

C -1.58239 -2.68963 0.

O -1.58239 0.83999 0.

H -0.16684 -1.19641 0.

H -4.12829 0.17569 0.

H -4.89825 -2.17462 0.

H -3.2169 -4.04598 0.

H -0.79023 -3.42886 0.

1+2

N 1.809617 -0.307392 -0.032040

C 1.820265 1.084940 -0.050901

C 3.118604 1.668743 0.011984

C 4.225842 0.865423 0.097413

C 4.148999 -0.534666 0.120559

C 2.895877 -1.108081 0.049180

O 0.739360 1.688276 -0.113516

H 0.882796 -0.751457 -0.049431

H 3.185478 2.748003 -0.002845

H 5.207037 1.327378 0.150103

H 5.032758 -1.155807 0.178465

N 2.656177 -2.453556 0.006627

H 1.716366 -2.765605 0.196507

H 3.384290 -3.054186 0.348688

N -1.733649 0.361383 -0.036559

C -1.727940 -1.021628 0.038150

C -3.030615 -1.620867 0.093177

C -4.158887 -0.856223 0.071573

C -4.087386 0.553210 -0.005967

C -2.851029 1.119399 -0.058249

O -0.656335 -1.644005 0.052965

H -0.815653 0.836792 -0.074359

H -3.069503 -2.700964 0.151459

H -5.130794 -1.337493 0.114284

H -4.974846 1.170189 -0.024147

H -2.687113 2.188746 -0.118788

1+3

N 1.7626 -0.29016 0.

C 1.80785 1.10306 0.

C 3.12656 1.64291 0.

C 4.21181 0.8074 0.

C 4.09904 -0.59287 0.

C 2.83086 -1.11023 0.

O 0.74119 1.73192 0.

H 0.82471 -0.71695 0.

H 3.22757 2.71941 0.

H 5.20661 1.24116 0.

H 4.9535 -1.25283 0.

O 2.60379 -2.42711 0.

H 1.65654 -2.61576 0.

N -1.73972 0.37099 0.

C -1.72793 -1.0128 0.

C -3.02371 -1.62215 0.

C -4.15684 -0.86446 0.

C -4.09382 0.54594 0.

C -2.86186 1.12248 0.

O -0.65111 -1.63097 0.

H -0.82728 0.85709 0.

H -3.05535 -2.70374 0.

H -5.12555 -1.3534 0.

H -4.98506 1.15699 0.

H -2.70439 2.1941 0.

2+2

N 1.739832 -0.237816 -0.033947

C 1.725490 1.153314 -0.018582

C 3.010360 1.760236 0.041408

C 4.134962 0.975609 0.094366

C 4.085670 -0.423950 0.085643

C 2.841540 -1.020126 0.015769

O 0.628527 1.737248 -0.051096

H 0.827990 -0.716298 -0.047054

H 3.057722 2.840532 0.053088

H 5.107330 1.455784 0.146559

H 4.981898 -1.028780 0.119135

N 2.624263 -2.365577 -0.052854

H 1.687786 -2.700905 0.116074

H 3.366100 -2.966689 0.256302

N -1.739832 0.237816 0.033947

C -1.725490 -1.153314 0.018582

C -3.010360 -1.760236 -0.041408

C -4.134962 -0.975609 -0.094366

C -4.085670 0.423950 -0.085643

C -2.841540 1.020126 -0.015769

O -0.628527 -1.737248 0.051096

H -0.827990 0.716298 0.047054

H -3.057722 -2.840532 -0.053088

H -5.107330 -1.455784 -0.146559

H -4.981898 1.028780 -0.119135

N -2.624263 2.365577 0.052854

H -1.687786 2.700905 -0.116074

H -3.366100 2.966689 -0.256302

3+3

N 1.69536 -0.26179 -0.0018

C 1.72574 1.12927 -0.00187

C 3.03189 1.68689 -0.00005

C 4.12975 0.8647 0.00183

C 4.03564 -0.53464 0.00207

C 2.77372 -1.06991 0.00019

O 0.64592 1.74796 -0.00351

H 0.77228 -0.72229 -0.00312

H 3.11911 2.76447 -0.00011

H 5.11811 1.31246 0.0033

H 4.89874 -1.18323 0.00367

O 2.56089 -2.38604 0.00023

H 1.61501 -2.58859 -0.00083

N -1.69536 0.26179 -0.0018

C -1.72574 -1.12927 -0.00187

C -3.03189 -1.68689 -0.00005

C -4.12975 -0.8647 0.00183

C -4.03564 0.53464 0.00207

C -2.77372 1.06991 0.00019

O -0.64592 -1.74796 -0.00351

H -0.77228 0.72229 -0.00312

H -3.11911 -2.76447 -0.00011

H -5.11811 -1.31246 0.0033

H -4.89874 1.18323 0.00367

O -2.56089 2.38604 0.00023

H -1.61501 2.58859 -0.00083

2+3

N 1.71861 -0.26462 -0.10296

C 1.71103 1.12573 -0.07337

C 2.99352 1.72707 0.0235

C 4.11412 0.93696 0.09558

C 4.06005 -0.46131 0.07265

C 2.81614 -1.05276 -0.03263

O 0.61552 1.7166 -0.12701

H 0.80903 -0.74387 -0.14646

H 3.04425 2.80688 0.04587

H 5.08652 1.41295 0.17561

H 4.95291 -1.06965 0.124

N 2.59493 -2.39487 -0.11599

H 1.65458 -2.73231 0.02299

H 3.33181 -3.0051 0.18641

N -1.70993 0.23833 -0.04021

C -1.74262 -1.15332 -0.02371

C -3.0533 -1.70559 0.03842

C -4.14664 -0.87883 0.08017

C -4.04754 0.52176 0.06486

C -2.78381 1.05081 0.0026

O -0.66741 -1.77337 -0.06297

H -0.78454 0.69308 -0.08659

H -3.14503 -2.78309 0.05099

H -5.13615 -1.32217 0.12777

H -4.9075 1.17423 0.09934

O -2.56407 2.36664 -0.01757

H -1.61736 2.56172 -0.05674

1'+1'

C 1.80256 0.98133 0.00707

N 1.66845 -0.34324 0.02879

C 3.05843 1.6056 -0.01506

C 2.77501 -1.09547 0.03164

C 4.18176 0.81298 -0.01235

H 3.11034 2.68641 -0.03393

C 4.05057 -0.57605 0.01229

H 2.613 -2.17009 0.05022

H 5.16531 1.26998 -0.02964

H 4.91305 -1.22968 0.01566

O 0.72058 1.7421 0.00557

H -0.10708 1.18817 0.0199

C -1.80256 -0.98133 0.00707

N -1.66845 0.34324 0.02879

C -3.05843 -1.6056 -0.01506

C -2.77501 1.09547 0.03164

C -4.18176 -0.81298 -0.01235

H -3.11034 -2.68641 -0.03393

C -4.05057 0.57605 0.01229

H -2.613 2.17009 0.05022

H -5.16531 -1.26998 -0.02964

H -4.91305 1.22968 0.01566

O -0.72058 -1.7421 0.00557

H 0.10708 -1.18817 0.0199

1'+2'

C -4.12473 0.06197 -0.02027

C -2.92716 -0.65425 -0.067

N -1.73203 -0.04797 -0.05488

C -1.68094 1.28505 -0.00516

C -2.82382 2.08514 0.04102

C -4.04786 1.44401 0.0341

O -0.49336 1.87499 0.00546

N -2.91929 -2.02498 -0.17492

H -5.07692 -0.45435 -0.03602

H -2.72441 3.16108 0.08211

H -4.96081 2.02912 0.07094

H 0.24259 1.21305 -0.02455

H -2.05811 -2.49436 0.05152

H -3.74904 -2.50825 0.11926

C 4.09379 -0.02207 -0.0013

C 2.91973 0.7 -0.03693

N 1.70535 0.13895 -0.03942

C 1.62306 -1.18889 -0.00684

C 2.75728 -2.01268 0.03143

C 3.99611 -1.41377 0.03407

O 0.42428 -1.7549 -0.01038

H 2.93618 1.78651 -0.06435

H 5.05177 0.482 -0.00089

H 2.63191 -3.08758 0.0565

H 4.89171 -2.02515 0.06288

H -0.29296 -1.06175 -0.04638

1'+3'

C -4.12256 0.02762 -0.04325

C -2.92187 -0.66752 -0.04425

N -1.72853 -0.07886 -0.02393

C -1.67249 1.25785 -0.00165

C -2.81963 2.05225 0.00155

C -4.04415 1.41206 -0.01958

O -0.48669 1.84753 0.01825

O -2.96176 -2.01123 -0.06677

H -5.06099 -0.50899 -0.06042

H -2.72264 3.12909 0.02006

H -4.9563 1.99896 -0.01782

H 0.25445 1.18979 0.01253

H -2.06471 -2.36153 -0.06622

C 4.11368 -0.00677 0.0278

C 2.93262 0.70448 0.02283

N 1.72421 0.13011 0.01014

C 1.6581 -1.19814 0.00171

C 2.79846 -2.01198 0.00575

C 4.03108 -1.39971 0.01902

O 0.46115 -1.77451 -0.01083

H 2.93745 1.79127 0.02935

H 5.06643 0.50686 0.03829

H 2.68398 -3.08827 -0.00151

H 4.93323 -2.00182 0.02254

H -0.25133 -1.08311 -0.01358

2'+2'

C 4.1148705314 -0.0861423858 -0.0356783626

C -4.1148705314 0.0861423858 0.0356783626

C 2.9311044934 0.6556814296 -0.0486950279

C -2.9311044934 -0.6556814296 0.0486950279

N 1.7255537599 0.0725233974 -0.0244713241

N -1.7255537599 -0.0725233974 0.0244713241

C 1.6493650567 -1.2585051776 0.0065898216

C -1.6493650567 1.2585051776 -0.0065898216

C 2.7730092315 -2.0838408858 0.0184003889

C -2.7730092315 2.0838408858 -0.0184003889

C 4.0103293745 -1.466158391 -0.001736562

C -4.0103293745 1.466158391 0.001736562

O 0.4420671387 -1.8139752577 0.0312755698

O -0.4420671387 1.8139752577 -0.0312755698

N 2.9472660101 2.0265831688 -0.1338163708

N -2.9472660101 -2.0265831688 0.1338163708

H 5.07768268 0.4095989206 -0.0599344472

H -5.07768268 -0.4095989206 0.0599344472

H 2.6537956399 -3.1582055341 0.0467751083

H -2.6537956399 3.1582055341 -0.0467751083

H 4.9117668749 -2.0700609713 0.0093828601

H -4.9117668749 2.0700609713 -0.0093828601

H -0.2655011828 -1.1180053679 0.0388013318

H 0.2655011828 1.1180053679 -0.0388013318

H 2.0966562256 2.5076942938 0.1072664682

H -2.0966562256 -2.5076942938 -0.1072664682

H 3.7903858661 2.492922489 0.1490048652

H -3.7903858661 -2.492922489 -0.1490048652

3'+3'

C -4.13926 0.04145 0.

C -2.94797 -0.67176 0.

N -1.74761 -0.09746 0.

C -1.6779 1.2371 0.

C -2.80854 2.04921 0.

C -4.0426 1.42374 0.

O -0.47301 1.80073 0.

O -3.00514 -2.01341 0.00001

H -5.08562 -0.4814 0.

H -2.69797 3.12487 -0.00001

H -4.94697 2.02264 -0.00001

H 0.2364 1.11274 0.

H -2.11194 -2.37399 0.00001

C 4.13926 -0.04145 0.

C 2.94797 0.67176 0.

N 1.74761 0.09746 0.

C 1.6779 -1.2371 0.

C 2.80854 -2.04921 0.

C 4.0426 -1.42374 0.

O 0.47301 -1.80073 0.

O 3.00514 2.01341 0.00001

H 5.08562 0.4814 0.

H 2.69797 -3.12487 -0.00001

H 4.94697 -2.02264 -0.00001

H -0.2364 -1.11274 0.

H 2.11194 2.37399 0.00001

2'+3'

C -4.13485 0.07167 0.07067

C -2.94422 -0.65968 0.04705

N -1.7449 -0.06345 0.0168

C -1.68474 1.26841 0.0015

C -2.81376 2.08361 0.01948

C -4.04456 1.45249 0.05621

O -0.47879 1.8332 -0.02776

N -2.94897 -2.03157 0.00835

H -5.09272 -0.43382 0.09081

H -2.70507 3.1593 0.00726

H -4.95165 2.04733 0.07359

H 0.22344 1.13861 -0.0297

H -2.08838 -2.50055 0.23737

H -3.78189 -2.4978 0.31947

C 4.11586 -0.05572 -0.00645

C 2.92985 0.66482 -0.04881

N 1.7253 0.1019 -0.02113

C 1.64156 -1.23051 0.05083

C 2.76822 -2.04973 0.09931

C 4.00706 -1.43543 0.06913

O 0.43495 -1.78332 0.0772

O 2.99771 2.00475 -0.12079

H 5.06661 0.45854 -0.03257

H 2.6492 -3.12303 0.15664

H 4.90625 -2.04103 0.10444

H -0.27816 -1.09305 0.03164

H 2.10694 2.37024 -0.1448

BSSE energy (a.u.)

1+10.000695332

1+20.000810585

1+30.000802243

2+20.000943014

2+30.001049643

3+30.001145138

1'+1'0.00114562

1'+2'0.001166664

1'+3'0.001180165

2'+2'0.00118465

2'+3'0.001191717

3'+3'0.00121304

S1