NDLI: Characteristics of the hydrogen bond and the structure of Н-complexes of p-n-propyloxybenzoic acid and p-n-propyloxy-p′-cyanobiphenyl

Content Provider	Springer Nature Link
Author	Giricheva, N. I. Fedorov, M. S. Shpilevaya, K. E. Syrbu, S. A. Ditsina, O. Yu.
Copyright Year	2017
Abstract	The conformational properties of p-n-propyloxybenzoic acid and p-n-propyloxy-p′-cyanobiphenyl molecules, which can exhibit liquid crystalline properties in the formation of Н-complexes, are studied (DFT/B3LYP)/cc-pVTZ method). It is found that a molecule of p-n-propyloxybenzoic acid has 16 conformers that can be divided into four groups with respect to relative energies (0 kcal/mol, 1.6 kcal/mol, 6.5 kcal/mol, and 8.1 kcal/mol), and a molecule of p-n-propyloxy-p′-cyanobiphenyl has six conformers with relative energies of 0 kcal/mol (two conformers, φ(С$_{Ph}$–O–C–C)=180°) and 1.6 kcal/mol (four conformers, φ(С$_{Ph}$–O–C–C)=64.4°). In all conformers of the 3-AOCB molecule, phenyl rings are turned at 35° relative to each other. A conformation with the planar arrangement of two rings has a higher energy by 1.5 kcal/mol. Barriers to the internal rotation of different groups are determined and it is established that the structural nonrigidity of the molecules is mainly due to the possible rotation of the–C$_{2}$Н$_{5}$ moiety about the C–C bond. It is shown that with increasing temperature the vibrational amplitudes of the OC$_{3}$H$_{7}$ substituent, which enhance the probabilities of transitions between the conformers, become appreciably larger. It is found that p-n-propyloxybenzoic acid and p-n-propyloxy-p′-cyanobiphenyl can form Н-complexes with the medium hydrogen bond. Two types of the structural organization of Н-complexes are considered: linear and angular. The similarity of energies of Н-complexes with different structures (NBO analysis) can be the reason for the occurrence of two liquid crystalline subphases of p-n-propyloxybenzoic acid and p-n-propyloxy-p′-cyanobiphenyl system.
Starting Page	9
Ending Page	16
Page Count	8
File Format	PDF
ISSN	00224766
Journal	Journal of Structural Chemistry
Volume Number	58
Issue Number	1
e-ISSN	15738779
Language	English
Publisher	Pleiades Publishing
Publisher Date	2017-03-23
Publisher Place	Moscow
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	liquid crystals p-n-propyloxybenzoic acid p-n-propyloxy-p′-cyanobiphenyl quantum chemical calculations NBO analysis conformers vibrational amplitudes Н-complexes hydrogen bond Inorganic Chemistry Physical Chemistry Atomic, Molecular, Optical and Plasma Physics Atomic/Molecular Structure and Spectra Solid State Physics
Content Type	Text
Resource Type	Article
Subject	Materials Chemistry Physical and Theoretical Chemistry Inorganic Chemistry

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