Optimization of the Selection of Chain Amine Scrubbers for the CO2 Capture
Mohammed J. Al-Marri1, Mahmoud M. Khader1, Emmanuel P. Giannelis2, and Mohamed F. Shibl1,2,3
(1) Gas Processing Center, College of Engineering, Qatar University, P.O. Box 2713 Doha, Qatar.
(2) Department of Materials Science and Engineering (MSE), Cornell University, Ithaca, NY 14853, USA.
(3) Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt.
Table S1. Stabilization energies [kcal/mol] of donor-acceptor interaction between compound c and CO2 in NBO Basis
Donor NBO / Acceptor NBO / E(2)LP (1) N1
LP (1) N1
LP (1) N1
LP (1) N1
LP (1) N1
LP (1) N1
BD (1) C24-O26
BD (3) C24-O26
BD (3) C24-O26
BD (3) C24-O26
BD (3) C24-O26
BD (3) C24-O26
LP (2) O25
LP (3) O25
LP (3) O25
BD* (3) C24-O26 / RY*(4) C24
RY*(1) O25
RY*(6) O25
RY*(2) O26
RY*(7) O26
BD*(3) C24-O26
RY*(2) N1
RY*(1) N1
RY*(2) N1
RY*(4) N1
RY*(5) N1
BD*(1) C20-H21
RY*(4) N1
BD*(1) C8-H10
BD*(1) C11-H13
RY*(1) N1 / 0.71
0.16
0.08
0.14
0.08
0.74
0.06
0.32
0.05
0.06
0.07
0.09
0.07
0.06
0.06
0.06
SUM=2.81
Table S2. Stabilization energies [kcal/mol] of donor-acceptor interaction between compound d and CO2 in NBO Basis
Donor NBO / Acceptor NBO / E(2)BD (1) N14-H15
LP (1) N14
LP (1) N14
LP (1) N14
LP (1) N14
LP (1) N14
LP (1) N14
LP (1) N14
LP (1) N14
BD (3) C24-O25
BD (3) C24-O25
BD (3) C24-O25
BD (1) C24-O26
LP (1) O25
LP (2) O26
BD*(3) C24-O25 / RY*(6) C24
RY*(4) C24
RY*(1) O25
RY*(3) O25
RY*(1) O26
BD*(1) C24-O25
BD*(2) C24-O25
BD*(3) C24-O25
BD*(1) C24-O26
RY*(1) H3
RY*(1) N14
BD*(1) C2-H3
RY*(3) N14
BD*(1) C2-H3
BD*(1) C8-N14
RY*(1) N14 / 0.05
0.18
0.23
0.09
0.19
0.06
0.05
1.84
0.06
0.06
0.08
0.20
0.05
0.17
0.05
0.08
SUM=3.44
Table S3. Stabilization energies [kcal/mol] of donor-acceptor interaction between compound e and CO2 in NBO Basis
Donor NBO / Acceptor NBO / E(2)BD (1) N1-H2
BD (1) N1-C3
BD (1) N1-C3
BD (1) N1-C6
BD (1) N1-C6
BD (1) N1-C6
BD (1) C3-H4
BD (1) C3-C9
BD (1) C9-H10
BD (1) C9-H11
BD (1) C9-H11
BD (1) C9-H11
BD (1) C9-H11
BD (1) C9-H11
BD (1) C9-H11
BD (1) C9-H11
BD (1) C12-H14
BD (1) C12-H14
BD (1) C12-H14
BD (1) C12-H14
BD (1) C12-H14
LP (1) N1
LP (1) N1
LP (1) N1
LP (1) N1
LP (1) N1
LP (1) N1
LP (1) N1
LP (1) N1
LP (1) N1
LP (1) N1
LP (1) N1
LP (1) N1
BD (1) C24-O25
BD (1) C24-O25
BD (1) C24-O25
BD (1) C24-O25
BD (1) C24-O25
BD (1) C24-O25
BD (2) C24-O25
BD (2) C24-O25
BD (2) C24-O25
BD (3) C24-O25
BD (3) C24-O25
BD (3) C24-O25
BD (3) C24-O25
BD (3) C24-O25
BD (3) C24-O25
BD (3) C24-O25
BD (1) C24-O26
BD (1) C24-O26
BD (1) C24-O26
BD (1) C24-O26
BD (1) C24-O26
BD (1) C24-O26
BD (2) C24-O26
BD (2) C24-O26
BD (2) C24-O26
BD (2) C24-O26
BD (2) C24-O26
BD (2) C24-O26
BD (2) C24-O26
BD (2) C24-O26
BD (2) C24-O26
BD (2) C24-O26
BD (2) C24-O26
CR (1) C24
CR (1) O25
CR (1) O26
LP (1) O25
LP (1) O25
LP (1) O25
LP (1) O25
LP (1) O26
LP (1) O26
LP (1) O26
LP (1) O26
LP (1) O26
LP (1) O26
LP (1) O26
LP (1) O26
LP (2) O26
LP (2) O26
LP (2) O26
LP (2) O26
LP (2) O26
LP (2) O26
BD*(2) C24-O25
BD*(2) C24-O25
BD*(2) C24-O25
BD*(3) C24-O25
BD*(3) C24-O25
BD*(3) C24-O25
BD*(2) C24-O26
BD*(2) C24-O26
BD*(2) C24-O26
BD*(2) C24-O26 / RY*(5) C24
RY*(1) C24
BD*(3) C24-O25
RY*(1) C24
RY*(5) C24
BD*(3) C24-O25
RY*(1) O26
RY*(1) O26
BD*(1) C24-O26
RY*(1) O26
RY*(2) O26
RY*(3) O26
RY*(4) O26
BD*(3) C24-O25
BD*(1) C24-O26
BD*(2) C24-O26
RY*(1) O25
RY*(2) O25
RY*(4) O25
BD*(1) C24-O25
BD*(3) C24-O25
RY*(3) C24
RY*(5) C24
RY*(10) C24
RY*(5) O25
RY*(2) O26
RY*(4) O26
RY*(5) O26
BD*(1) C24-O25
BD*(2) C24-O25
BD*(3) C24-O25
BD*(1) C24-O26
BD*(2) C24-O26
RY*(1) N1
RY*(1) C6
RY*(3) C6
RY*(1) H14
BD*(1) C9-H11
BD*(1) C12-H14
RY*(3) C6
BD*(1) C6-H7
BD*(1) C6-H8
RY*(1) N1
RY*(9) N1
RY*(1) H14
BD*(1) N1-H2
BD*(1) C6-H8
BD*(1) C12-H14
BD*(1) C12-N17
RY*(1) N1
RY*(2) N1
RY*(1) C3
RY*(1) H11
BD*(1) C9-H11
BD*(1) C12-H14
RY*(1) N1
RY*(1) C3
RY*(3) C3
RY*(5) C3
RY*(1) H4
RY*(10) C9
RY*(1) H11
BD*(1) N1-C3
BD*(1) C3-H4
BD*(1) C3-H5
BD*(1) C9-H11
BD*(1) C9-H11
BD*(1) C12-H14
BD*(1) C9-H11
RY*(1) H14
BD*(1) C9-H11
BD*(1) C12-H14
BD*(1) C12-N17
RY*(9) C9
RY*(11) C9
RY*(1) H11
BD*(1) C3-H5
BD*(1) C9-H10
BD*(1) C9-H11
BD*(1) C9-N15
BD*(1) C12-H14
RY*(1) N1
RY*(1) H11
BD*(1) N1-C6
BD*(1) C3-H5
BD*(1) C9-H11
BD*(1) C9-N15
RY*(3) C6
RY*(5) C6
RY*(3) N15
RY*(1) N1
BD*(1) N1-H2
BD*(1) C12-H14
RY*(1) C3
RY*(3) C3
RY*(5) C3
RY*(11) C3 / 0.05
0.09
0.15
0.06
0.07
0.12
0.06
0.09
0.05
0.85
0.26
0.27
0.13
0.10
0.69
0.15
0.46
0.12
0.20
0.23
1.03
0.08
0.13
0.05
0.05
0.08
0.15
0.09
0.25
0.07
10.81
0.51
0.23
0.10
0.10
0.05
0.12
0.08
0.32
0.05
0.06
0.06
0.19
0.07
1.04
0.06
0.18
2.10
0.16
0.33
0.09
0.09
0.38
0.40
0.10
0.13
0.24
0.07
0.06
0.06
0.07
0.30
0.06
0.08
0.12
0.07
0.06
0.30
0.50
0.15
0.06
5.85
0.05
0.06
0.08
0.25
0.11
0.14
9.81
0.14
0.06
0.05
0.52
0.05
0.38
1.95
0.30
0.10
0.09
0.11
0.16
0.06
0.37
0.44
0.10
0.12
0.08
SUM=47.62
Table S4. Stabilization energies [kcal/mol] of donor-acceptor interaction between compound f and CO2 in NBO Basis
Donor NBO / Acceptor NBO / E(2)LP (1) N15
LP (1) N15
LP (1) N15
LP (1) N15
LP (1) N15
LP (1) N15
LP (1) N15
BD (3) C24-O25
BD (3) C24-O25
BD (1) C24-O26
LP (1) O25
BD* (3) C24-O25 / RY*(4) C24
RY*(1) O25
RY*(3) O25
RY*(1) O26
RY*(6) O26
BD*(3) C24-O25
BD*(1) C24-O26
RY*(1) N15
BD*(1) C3-H4
RY*(2) N15
BD*(1) C3-H4
RY*(1) N15 / 0.35
0.17
0.07
0.13
0.06
1.56
0.06
0.12
0.15
0.11
0.15
0.10
SUM=3.03
Table S5. Stabilization energies [kcal/mol] of donor-acceptor interaction between compound g and CO2 in NBO Basis
Donor NBO / Acceptor NBO / E(2)LP (1) N15
LP (1) N15
LP (1) N15
LP (1) N15
LP (1) N15
LP (1) N15
LP (1) N15
BD (3) C20-O21
BD (3) C20-O21
BD (3) C20-O21
LP (1) O21
BD*(3) C20-O21 / RY*(4) C20
RY*(1) O21
RY*(3) O21
RY*(1) O22
BD*(1) C20-O21
BD*(3) C20-O21
BD*(1) C20-O22
RY*(1) H4
RY*(1) N15
BD*(1) C3-H4
BD*(1) C3-H4
RY*(1) N15 / 0.19
0.23
0.08
0.19
0.06
1.78
0.06
0.05
0.08
0.18
0.21
0.08
SUM=3.19
Table S6. Stabilization energies [kcal/mol] of donor-acceptor interaction between compound h and CO2 in NBO Basis
Donor NBO / Acceptor NBO / E(2)LP (1) N1
LP (1) N1
LP (1) N1
LP (1) N1
LP (1) N1
LP (1) N1
LP (1) N1
BD (3) C23-O24
BD (3) C23-O24
BD (3) C23-O24
LP (1) O24
LP (1) O25
LP (2) O25
LP (3) O25
BD*(3) C23-O24 / RY*(4) C23
RY*(1) O24
RY*(5) O24
RY*(1) O25
RY*(3) O25
BD*(2) C23-O24
BD*(3) C23-O24
RY*(1) N1
RY*(1) H14
BD*(1) C12-H14
BD*(1) C12-H14
BD*(1) C9-H11
BD*(1) C9-H11
BD*(1) C9-H11
RY*(1) N1 / 0.33
0.15
0.06
0.09
0.06
0.27
0.78
0.08
0.09
0.34
0.24
0.18
0.23
0.17
0.06
SUM=3.13
Table S7. Stabilization energies [kcal/mol] of donor-acceptor interaction between compound i and CO2 in NBO Basis
Donor NBO / Acceptor NBO / E(2)LP (1) N15
LP (1) N15
LP (1) N15
LP (1) N15
LP (1) N15
LP (1) N15
LP (1) N15
BD (1) C23-O24
BD (1) C23-O24
BD (3) C23-O24
BD (3) C23-O24
BD (3) C23-O24
BD (1) C23-O25
BD (1) C23-O25
LP (1) O24
LP (3) O25
LP (3) O25
LP (3) O25
BD*(3) C23-O24 / RY*(4) C23
RY*(1) O24
RY*(2) O25
RY*(3) O25
RY*(6) O25
BD*(2) C23-O24
BD*(3) C23-O24
RY*(1) N15
RY*(2) N15
RY*(1) H4
RY*(1) N15
BD*(1) C3-H4
RY*(1) N15
RY*(2) N15
BD*(1) C3-H4
RY*(1) N15
RY*(2) N15
BD*(1) C26-H27
RY*(1) N15 / 0.59
0.20
0.08
0.10
0.06
0.06
1.26
0.05
0.06
0.07
0.30
0.26
0.06
0.10
0.23
0.08
0.05
0.06
0.10
SUM=3.77
Table S8. Stabilization energies [kcal/mol] of donor-acceptor interaction between compound j and CO2 in NBO Basis
Donor NBO / Acceptor NBO / E(2)BD (1) N15-H16
LP (1) N15
LP (1) N15
LP (1) N15
LP (1) N15
LP (1) N15
LP (1) N15
LP (1) N15
BD (3) C19-O20
BD (3) C19-O20
BD (1) C19-O21
LP (1) O20
BD*(3) C19-O20 / RY*(6) C19
RY*(4) C19
RY*(1) O20
RY*(3) O20
RY*(1) O21
BD*(1) C19-O20
BD*(3) C19-O20
BD*(1) C19-O21
RY*(1) N15
BD*(1) C3-H4
RY*(3) N15
BD*(1) C3-H4
RY*(1) N15 / 0.05
0.19
0.23
0.08
0.19
0.06
1.81
0.06
0.08
0.16
0.05
0.17
0.08
SUM=3.21
Table S9. Stabilization energies [kcal/mol] of donor-acceptor interaction between compound k and CO2 in NBO Basis
Donor NBO / Acceptor NBO / E(2)LP (1) N1
LP (1) N1
LP (1) N1
LP (1) N1
LP (1) N1
LP (1) N1
BD (3) C23-O24
BD (3) C23-O24
BD (3) C23-O24
LP (1) O25
LP (2) O25
BD*(3) C23-O24 / RY*(4) C23
RY*(2) O24
RY*(6) O24
RY*(1) O25
RY*(6) O25
BD*(3) C23-O24
RY*(1) N1
RY*(5) N1
BD*(1) C26-H29
BD*(1) C8-H10
BD*(1) C8-H10
RY*(1) N1 / 0.66
0.13
0.08
0.16
0.08
0.83
0.35
0.10
0.08
0.06
0.16
0.06
SUM=2.75
Table S10. Stabilization energies [kcal/mol] of donor-acceptor interaction between compound l and CO2 in NBO Basis
Donor NBO / Acceptor NBO / E(2)LP (1) N14
LP (1) N14
LP (1) N14
LP (1) N14
LP (1) N14
LP (1) N14
LP (1) N14
BD (3) C23-O24
BD (3) C23-O24
BD (3) C23-O24
BD (1) C23-O25
LP (1) O24
BD*(3) C23-O24
BD*(3) C23-O24 / RY*(4) C23
RY*(1) O24
RY*(3) O24
RY*(1) O25
RY*(6) O25
BD*(3) C23-O24
BD*(1) C23-O25
RY*(1) H3
RY*(1) N14
BD*(1) C2-H3
RY*(2) N14
BD*(1) C2-H3
RY*(1) N14
BD*(1) C2-H3 / 0.33
0.16
0.10
0.11
0.05
1.54
0.06
0.09
0.11
0.25
0.11
0.23
0.10
0.05
SUM=3.29
Table S11. Stabilization energies [kcal/mol] of donor-acceptor interaction between compound m and CO2 in NBO Basis
Donor NBO / Acceptor NBO / E(2)BD (1) N14-H15
LP (1) N14
LP (1) N14
LP (1) N14
LP (1) N14
LP (1) N14
LP (1) N14
LP (1) N14
BD (3) C18-O19
BD (3) C18-O19
BD (3) C18-O19
LP (1) O19
BD*(3) C18-O19
BD*(3) C18-O19 / RY*(6) C18
RY*(4) C18
RY*(1) O19
RY*(3) O19
RY*(1) O20
BD*(1) C18-O19
BD*(3) C18-O19
BD*(1) C18-O20
RY*(1) H3
RY*(1) N14
BD*(1) C2-H3
BD*(1) C2-H3
RY*(1) N14
BD*(1) C2-H3 / 0.05
0.18
0.22
0.09
0.19
0.06
1.79
0.06
0.08
0.08
0.22
0.20
0.08
0.05
SUM=3.35
Table S12. Stabilization energies [kcal/mol] of donor-acceptor interaction between compound n and CO2 in NBO Basis
Donor NBO / Acceptor NBO / E(2)LP (1) N1
LP (1) N1
LP (1) N1
LP (1) N1
LP (1) N1
LP (1) N1
BD (3) C22-O24
BD (3) C22-O24
BD (3) C22-O24
LP (2) O23
BD*(3) C22-O24 / RY*(4) C22
RY*(1) O23
RY*(6) O23
RY*(2) O24
RY*(6) O24
BD*(3) C22-O24
RY*(1) N1
RY*(5) N1
BD*(1) C18-H19
BD*(1) C8-H10
RY*(1) N1 / 0.62
0.14
0.06
0.11
0.06
0.72
0.32
0.11
0.08
0.16
0.06
SUM=2.44
Table S13. Stabilization energies [kcal/mol] of donor-acceptor interaction between compound o and CO2 in NBO Basis
Donor NBO / Acceptor NBO / E(2)LP (1) N14
LP (1) N14
LP (1) N14
LP (1) N14
LP (1) N14
LP (1) N14
LP (1) N14
LP (1) N14
BD (1) C22-O23
BD (3) C22-O23
BD (3) C22-O23
BD (3) C22-O23
BD (1) C22-O24
BD (1) C22-O24
LP (1) O23
LP (3) O24
LP (3) O24
LP (3) O24
LP (3) O24
BD*(3) C22-O23 / RY*(4) C22
RY*(1) O23
RY*(3) O23
RY*(2) O24
RY*(3) O24
RY*(6) O24
BD*(2) C22-O23
BD*(3) C22-O23
RY*(2) N14
RY*(1) H3
RY*(1) N14
BD*(1) C2-H3
RY*(1) N14
RY*(2) N14
BD*(1) C2-H3
RY*(1) N14
RY*(2) N14
RY*(7) N14
BD*(1) C26-H27
RY*(1) N14 / 0.55
0.16
0.07
0.08
0.08
0.05
0.08
1.25
0.05
0.11
0.29
0.32
0.07
0.09
0.25
0.09
0.05
0.06
0.06
0.11
SUM=3.87
Table S14. Stabilization energies [kcal/mol] of donor-acceptor interaction between compound p and CO2 in NBO Basis
Donor NBO / Acceptor NBO / E(2)BD (1) N14-H15
LP (1) N14
LP (1) N14
LP (1) N14
LP (1) N14
LP (1) N14
LP (1) N14
LP (1) N14
BD (3) C18-O19
BD (3) C18-O19
BD (3) C18-O19
LP (1) O19
BD* (3) C18-O19
BD* (3) C18-O19 / RY*(6) C18
RY*(4) C18
RY*(1) O19
RY*(3) O19
RY*(1) O20
BD*(1) C18-O19
BD*(3) C18-O19
BD*(1) C18-O20
RY*(1) H3
RY*(1) N14
BD*(1) C2-H3
BD*(1) C2-H3
RY*(1) N14
BD*(1) C2-H3 / 0.05
0.17
0.23
0.10
0.18
0.06
1.80
0.06
0.09
0.08
0.24
0.22
0.08
0.05
SUM=3.41
Table S15. Stabilization energies [kcal/mol] of donor-acceptor interaction between OH-substituted analogue of compound c and CO2 in NBO Basis
Donor NBO / Acceptor NBO / E(2)BD (1) O23-H24
LP (1) N1
LP (1) N1
LP (1) N1
LP (1) N1
LP (1) N1
LP (1) N1
LP (1) N1
LP (1) N1
LP (1) O23
BD (1) C20-O21
BD (1) C20-O21
BD (1) C20-O22
BD (3) C20-O22
LP (1) O21
LP (2) O21
LP (2) O21
BD*(3) C20-O22 / RY*(4) C20
RY*(4) C20
RY*(2) O21
RY*(3) O21
RY*(7) O21
RY*(1) O22
RY*(6) O22
BD*(1) C20-O21
BD*(3) C20-O22
BD*(1) C20-O21
RY*(1) N1
BD*(1) O23-H24
RY*(7) N1
RY*(1) N1
BD*(1) O23-H24
RY*(2) H24
BD*(1) O23-H24
RY*(1) N1 / 0.06
0.59
0.06
0.10
0.06
0.25
0.08
0.07
1.37
0.05
0.10
0.06
0.08
0.14
1.32
0.16
2.10
0.13
SUM=6.78
Table S16. Stabilization energies [kcal/mol] of donor-acceptor interaction between OH-substituted analogue of compound d and CO2 in NBO Basis
Donor NBO / Acceptor NBO / E(2)LP (1) N14
LP (1) N14
LP (1) N14
LP (1) N14
LP (1) N14
LP (1) N14
LP (1) N14
BD (3) C20-O21
BD (3) C20-O21
BD (3) C20-O21
BD (1) C20-O22
LP (1) O21
BD*(3) C20-O21
BD*(3) C20-O21 / RY*(4) C20
RY*(1) O21
RY*(3) O21
RY*(1) O22
BD*(1) C20-O21
BD*(3) C20-O21
BD*(1) C20-O22
RY*(1) H3
RY*(1) N14
BD*(1) C2-H3
RY*(3) N14
BD*(1) C2-H3
RY*(1) N14
BD*(1) C2-H3 / 0.19
0.23
0.09
0.19
0.06
1.83
0.06
0.08
0.08
0.22
0.05
0.24
0.08
0.06
SUM=3.46
Table S17. Stabilization energies [kcal/mol] of donor-acceptor interaction between OH-substituted analogue of compound e and CO2 in NBO Basis