TY - JOUR

T1 - X-ray and vibrational analysis of amino and chloro bibenzyl 4,4′-derivatives supported by quantum chemical calculations

AU - Smirnov, A.N.

AU - Odintsova, Olga V.

AU - Starova, Galina L.

AU - Solovyeva, Elena V.

PY - 2020/2/15

Y1 - 2020/2/15

N2 - Two derivatives of bibenzyl, 4,4′-diaminobibenzyl and 4,4′-dichlorobibenzyl, were studied for the first time by X-ray diffraction and vibrational spectroscopy in this work. The vibrational assignment was made in detail using Raman and IR measurements accompanied by DFT simulations performed in hybrid B3LYP version employing 6-31G (d,p) basis set. The normal modes interpretation was carried out on the basis of a potential energy distribution obtained by VEDA program. The structural diversity, consisting in the existence of eight crystallographically independent structures, is observed for DCBB while only one structure was revealed in crystal of DABB. This difference is attributed to the stabilization effect provided by intermolecular interactions between the amino groups and water molecules included in the crystalline structure of DABB. Trustworthy shortening of C (sp3)-C (sp3) bond length in ethane fragment was established in the crystal structures of both compounds and is explained by torsional vibration of C—Ph bonds. The characteristic vibrational modes of ethane fragment were assigned in the experimental Raman and IR spectra. The vibrations with participation of functional groups were also distinguished in the measured spectra. The obtained new data about bibenzyl derivatives could contribute in a better understanding of physical chemistry of compounds with freedom of rotation around the central C–C bond that is significant for targeted development of nanomachines and other prospective molecular systems.

AB - Two derivatives of bibenzyl, 4,4′-diaminobibenzyl and 4,4′-dichlorobibenzyl, were studied for the first time by X-ray diffraction and vibrational spectroscopy in this work. The vibrational assignment was made in detail using Raman and IR measurements accompanied by DFT simulations performed in hybrid B3LYP version employing 6-31G (d,p) basis set. The normal modes interpretation was carried out on the basis of a potential energy distribution obtained by VEDA program. The structural diversity, consisting in the existence of eight crystallographically independent structures, is observed for DCBB while only one structure was revealed in crystal of DABB. This difference is attributed to the stabilization effect provided by intermolecular interactions between the amino groups and water molecules included in the crystalline structure of DABB. Trustworthy shortening of C (sp3)-C (sp3) bond length in ethane fragment was established in the crystal structures of both compounds and is explained by torsional vibration of C—Ph bonds. The characteristic vibrational modes of ethane fragment were assigned in the experimental Raman and IR spectra. The vibrations with participation of functional groups were also distinguished in the measured spectra. The obtained new data about bibenzyl derivatives could contribute in a better understanding of physical chemistry of compounds with freedom of rotation around the central C–C bond that is significant for targeted development of nanomachines and other prospective molecular systems.

KW - Bibenzyls

KW - Crystal structure

KW - DFT

KW - IR spectroscopy

KW - PED

KW - Raman scattering

KW - BEHAVIOR

KW - ANILINE

KW - COMPLEXES

KW - ELECTRONIC-STRUCTURES

KW - BOND-LENGTH

KW - SPECTROSCOPY

KW - ASSIGNMENT

KW - SPECTRA

KW - DERIVATIVES

KW - 1,2-DIPHENYLETHANE

UR - http://www.scopus.com/inward/record.url?scp=85075525343&partnerID=8YFLogxK

UR - http://www.mendeley.com/research/xray-vibrational-analysis-amino-chloro-bibenzyl-44derivatives-supported-quantum-chemical-calculation

U2 - 10.1016/j.molstruc.2019.127287

DO - 10.1016/j.molstruc.2019.127287

M3 - Article

AN - SCOPUS:85075525343

VL - 1202

SP - 127287

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

SN - 0022-2860

M1 - 127287

ER -