Hydrogen and halogen bonding patterns and π–π aromatic interactions of some 6,7-disubstituted 1,3-benzothiazoles studied by X-ray diffraction and DFT calculations
| Autor: | Livio Racane, Gordana Pavlović, Zlatko Mihalić, Vesna Tralić-Kulenović, Marijana Đaković, Helena Čičak |
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| Rok vydání: | 2010 |
| Předmět: |
chemistry.chemical_classification
7-disubstituted 1 3-benzothiazoles hydrogen bonds halogen bonds pi–pi interactions X-ray structure DFT calculations AIM analysis Halogen bond Hydrogen Hydrogen bond Organic Chemistry Intermolecular force chemistry.chemical_element Analytical Chemistry Inorganic Chemistry Crystallography chemistry Computational chemistry Intramolecular force X-ray crystallography Halogen Non-covalent interactions Spectroscopy |
| Zdroj: | Journal of Molecular Structure. 975:115-127 |
| ISSN: | 0022-2860 |
| DOI: | 10.1016/j.molstruc.2010.04.005 |
| Popis: | The structures of five 6, 7-disubstituted 1, 3-benzothiazole (1, 3-benzothiazole = bta) derivatives: 6-chloro-7-nitro-bta (3), 6-iodo-7-nitro-bta (5), 6-amino-7-iodo-bta (6), 6-acetylamino-7-iodo-bta (7) and 6-amino-7-bromo-bta (8) are reported and investigated by X-ray crystallography and DFT calculations. The crystal structures of 3 and 5–8 are characterized by (i) relatively weak C—H...O/N/Br and N—H...O/N/S hydrogen bonds, (ii) C—Cl...O and C—I...O/N halogen bonds and Br...Br interactions and (iii) pi–pi interactions. DFT optimized structures of 3, 5, 6 and 8 are in a good agreement with the corresponding X-ray molecular data. Calculated structure of 7 deviates from the experimental geometry because of more favourable intermolecular hydrogen bonding in crystal phase compared to the weak intramolecular hydrogen bond in the gas phase. The molecular electrostatic potential maps were used for predicting possible hydrogen and halogen bonding sites in structures of 3, 5, 6 and 8, and AIM analysis in order to characterize the nature and strength of intermolecular interactions in all of the examined crystal structures. Experimental results agree well with AIM analysis suggesting that the detected hydrogen and halogen bonds are weak and mostly of electrostatic origin. |
| Databáze: | OpenAIRE |
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