Monatshefte Fur Chemie-Chemical Monthly

Monatshefte fur Chemie-Chemical Monthly

Supplementary Material

associated with the paper

The hydrogen bond interactions in glycine-nitrosamine complexes: A DFT Study

Batoul Makiabadi1.Hamideh Kian2

1Department of Chemical Engineering, Sirjan University of Technology, Sirjan, Iran

2Department of Chemistry, Payam Noor University, Tehran, Iran

Table of Contents Page

Table S1.Barrier hight (kJ/mol) values to the proton transfer for GNA1 and GNA2 complexes 2

Table S2. The structural parameters for GNA1-8 complexes 3

Fig S1. Relationship between B3LYP/6-311++G(df,pd) calculated interaction energy and sum of the NHNA…N(O)G and O(N)NA…HXG(X=C,N or O) distances (R) in GNA1-8 cyclic complexes 4

Fig S2.Relationship between sum of the H-bonds distances and sum of the 1hJ(NHNA… Y) and1hJ(HXG…Y) SSCCs in GNA1-8 complexes 5

Fig S3.Relationship between IE and sum of the 1hJ(NHNA…Y) and1hJ(HXG…Y) SSCCs in GNA1-8 complexes 6

Table S1 Barrier hight (kJ/mol) values to the proton transfer for GNA1 and GNA2 complexes.
ΔEele# / ΔE0 / ΔE0# / ΔH# / ΔG#
B3LYP/6-311++G(2d,2p)
GNA1→TS / 43.62 / 27.32 / 24.36 / 24.36 / 30.69
GNA2→TS / 60.06 / 45.3 / 41.75 / 41.75 / 50.38
B3LYP/6-311++G(df,pd)
GNA1→TS / 46.39 / 29.06 / 26.12 / 26.12 / 32.43
GNA2→TS / 61.59 / 46.33 / 42.85 / 42.85 / 51.26
B3LYP/aug-cc-pVDZ
GNA1→TS / 41.89 / 24.71 / 22.05 / 22.05 / 27.42
GNA2→TS / 56.92 / 41.77 / 38.48 / 38.49 / 46.07
B3PW91/6-311++G(2d,2p)
GNA1→TS / 36.44 / 20.82 / 17.96 / 17.96 / 24.11
GNA2→TS / 50.16 / 36 / 13.05 / 13.05 / 25.42
B3PW91/6-311++G(df,pd)
GNA1→TS / 37.68 / 26.41 / 20.04 / 18.79 / 21.15
GNA2→TS / 52.05 / 37.41 / 34.04 / 34.04 / 42.06
B3PW91/aug-cc-pVDZ
GNA1→TS / 19.03 / 16.44 / 16.44 / 21.83 / 35.47
GNA2→TS / 47.91 / 33.37 / 30.17 / 30.17 / 37.57
∆E0#= ∆Eele# + ZPE, ∆E# = ∆E0# + Ethermal, ∆H# = enthalpy of activation, ∆G# = Gibbs free energy of activation
Table S2 The structural parameters for GNA1-8 complexes.
Parameter / GNA1 / GNA2 / GNA3 / GNA4
O-H...O / 1.757 (175.2)
N-H...O / 1.843 (171.2) / 1.926 (148.1) / 1.941 (172.8)a
2.192 (170.3)b / 1.923 (166.5)
O-H...N / 1.895 (169.0)
N-H...N / 2.395 (156.5)
O-H / 0.992
0.969c / 0.99
N-H / 1.033
1.013C / 1.021 / 1.026a
1.016b / 1.017a
1.015b
Parameter / GNA5 / GNA6 / GNA7 / GNA8
N-H...O / 2.111 (176.7) / 2.083 (162.3)
O-H...N
N-H...N / 1.979 (171.3) / 2.353 (163.9)
C-H...O / 2.46 (162.5) / 2.078 (138.6)
C-H...N / 2.723 (149.3) / 2.748 (126.7)
N-H / 1.021
1.033c / 1.012 / 1.036 / 1.027
C-H / 1.094 (1.094) / 1.094 / 1.095 / 1.093
Angle values are given in parentheses
a Data for N13-H
b Data for N6-H10
c Data for monomers

Fig. S1 Relationship between B3LYP/6-311++G(df,pd) calculated interaction energy and sum of the NHNA…N(O)G and O(N)NA…HXG(X=C,N or O) distances (R) in GNA1-8 cyclic complexes

Fig. S2 Relationship between sum of the H-bonds distances and sum of the 1hJ(NHNA… Y) and1hJ(HXG…Y) SSCCs in GNA1-8 complexes.

Fig. S3 Relationship between IE and sum of the 1hJ(NHNA…Y) and1hJ(HXG…Y) SSCCs in GNA1-8 complexes.