کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1409924 1501839 2010 13 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
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
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
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
چکیده انگلیسی

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 CH⋯O/N/Br and NH⋯O/N/S hydrogen bonds, (ii) CCl⋯O and CI⋯O/N halogen bonds and Br⋯Br interactions and (iii) π–π 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.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Journal of Molecular Structure - Volume 975, Issues 1–3, 30 June 2010, Pages 115–127
نویسندگان
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