Hydrogen and halogen bonding patterns and pi–pi aromatic interactions of some 6, 7-disubstituted 1, 3-benzothiazoles studied by X-ray diffraction and DFT calculations (CROSBI ID 162379)
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Podaci o odgovornosti
Čičak, Helena ; Đaković, Marijana ; Mihalić, Zlatko ; Pavlović, Gordana ; Racané, Livio ; Tralić-Kulenović, Vesna
engleski
Hydrogen and halogen bonding patterns and pi–pi aromatic interactions of some 6, 7-disubstituted 1, 3-benzothiazoles studied by X-ray diffraction and DFT calculations
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.
6; 7-disubstituted 1; 3-benzothiazoles; hydrogen bonds; halogen bonds; pi–pi interactions; X-ray structure; DFT calculations; AIM analysis
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Podaci o izdanju
975 (1/3)
2010.
115-127
objavljeno
0022-2860
10.1016/j.molstruc.2010.04.005
Povezanost rada
Kemija, Tekstilna tehnologija