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 | |
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.