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Pregled bibliografske jedinice broj: 461386

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


Čičak, Helena; Đaković, Marijana; Mihalić, Zlatko; Pavlović, Gordana; Racané, Livio; Tralić-Kulenović, Vesna
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 // Journal of molecular structure, 975 (2010), 1/3; 115-127 doi:10.1016/j.molstruc.2010.04.005 (međunarodna recenzija, članak, znanstveni)


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Naslov
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

Autori
Čičak, Helena ; Đaković, Marijana ; Mihalić, Zlatko ; Pavlović, Gordana ; Racané, Livio ; Tralić-Kulenović, Vesna

Izvornik
Journal of molecular structure (0022-2860) 975 (2010), 1/3; 115-127

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
6; 7-disubstituted 1; 3-benzothiazoles; hydrogen bonds; halogen bonds; pi–pi interactions; X-ray structure; DFT calculations; AIM analysis

Sažetak
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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Tekstilna tehnologija



POVEZANOST RADA


Projekti:
117-0000000-3283 - Istraživanje novih višenamjenskih bojila i optičkih bjelila (Racane, Livio, MZOS ) ( POIROT)
119-1191342-1339 - Molekulsko modeliranje strukture i reaktivnosti organskih spojeva (Mihalić, Zlatko, MZOS ) ( POIROT)
119-1193079-1332 - Kemija metalnih kompleksa u reakcijama od biološkog značaja i novim materijalima (Popović, Zora, MZOS ) ( POIROT)

Ustanove:
Tekstilno-tehnološki fakultet, Zagreb,
Prirodoslovno-matematički fakultet, Zagreb

Citiraj ovu publikaciju

Čičak, Helena; Đaković, Marijana; Mihalić, Zlatko; Pavlović, Gordana; Racané, Livio; Tralić-Kulenović, Vesna
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 // Journal of molecular structure, 975 (2010), 1/3; 115-127 doi:10.1016/j.molstruc.2010.04.005 (međunarodna recenzija, članak, znanstveni)
Čičak, H., Đaković, M., Mihalić, Z., Pavlović, G., Racané, L. & Tralić-Kulenović, V. (2010) 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. Journal of molecular structure, 975 (1/3), 115-127 doi:10.1016/j.molstruc.2010.04.005.
@article{article, year = {2010}, pages = {115-127}, DOI = {10.1016/j.molstruc.2010.04.005}, keywords = {6, 7-disubstituted 1, 3-benzothiazoles, hydrogen bonds, halogen bonds, pi–pi interactions, X-ray structure, DFT calculations, AIM analysis}, journal = {Journal of molecular structure}, doi = {10.1016/j.molstruc.2010.04.005}, volume = {975}, number = {1/3}, issn = {0022-2860}, title = {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}, keyword = {6, 7-disubstituted 1, 3-benzothiazoles, hydrogen bonds, halogen bonds, pi–pi interactions, X-ray structure, DFT calculations, AIM analysis} }
@article{article, year = {2010}, pages = {115-127}, DOI = {10.1016/j.molstruc.2010.04.005}, keywords = {6, 7-disubstituted 1, 3-benzothiazoles, hydrogen bonds, halogen bonds, pi–pi interactions, X-ray structure, DFT calculations, AIM analysis}, journal = {Journal of molecular structure}, doi = {10.1016/j.molstruc.2010.04.005}, volume = {975}, number = {1/3}, issn = {0022-2860}, title = {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}, keyword = {6, 7-disubstituted 1, 3-benzothiazoles, hydrogen bonds, halogen bonds, pi–pi interactions, X-ray structure, DFT calculations, AIM analysis} }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


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