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. 2021 Feb 16;125(7):1526–1539. doi: 10.1021/acs.jpca.0c11183

Table 2. Geometrical Parameters (in Å) of the Intra- and Intermolecular Hydrogen Bondsa.

  intramolecular (o-substituent)
intermolecular (COOH or CONH2 group)
compd O/S–H H···O O/S···O O/N–H H···O O/N···O
Monomers
benzamide       1.007    
benzoic acid       0.964    
salicylamide 0.982 1.698 2.575 1.007    
2-mercaptobenzamide 1.346 2.000 3.107 1.007    
salicylic acid 0.975 1.772 2.628 0.964    
thiosalicylic acid 1.346 1.908 3.034 0.964    
salicylamide 0.958   2.995 1.007    
2-mercaptobenzamide 1.346   2.833 1.007    
salicylic acid 0.959   2.698 0.963    
thiosalicylic acid 1.347   2.739 0.964    
Dimers
benzamide       1.025 1.841 2.864
benzoic acid       0.994 1.659 2.653
salicylamide 0.981 1.691 2.569 1.024 1.846 2.869
2-mercaptobenzamide 1.345 2.020 3.123 1.025 1.848 2.871
salicylic acid 0.974 1.766 2.620 0.993 1.667 2.660
thiosalicylic acid 1.343 1.914 3.030 0.991 1.674 2.665
salicylamide 0.958   2.985 1.026 1.843 2.865
2-mercaptobenzamide 1.346   2.834 1.025 1.841 2.862
salicylic acid 0.959   2.677 0.994 1.661 2.665
thiosalicylic acid 1.347   2.715 0.993 1.664 2.657
a

O–H or S–H or N–H bond lengths as well as the H···O and O···O or S···O or N···O distances are included. Results for systems with closed ring by intramolecular hydrogen bond are bolded. Results for systems without intramolecular hydrogen bond are presented in the normal mode.