Synthesis, characterization, crystal structure determination and computational study of the two new bidentate O, N Schiff bases derived from bromosalicylaldehyde and amines containing alkyl halide pendant groups

被引：25
作者：
Grivani, Gholamhossein [1 ]
Tahmasebi, Vida [1 ]
Eskandari, Keiamars [2 ]
Khalaji, Aliakbar Dehno [3 ]
Bruno, Giuseppe [4 ]
Rudbari, Hadi Amiri [5 ]
机构：
[1] Damghan Univ, Sch Chem, Damghan, Iran
[2] Isfahan Univ Technol, Dept Chem, Esfahan, Iran
[3] Golestan Univ, Fac Sci, Dept Chem, Gorgan, Iran
[4] Univ Messina, Dip Sci Chim, I-98166 Messina, Italy
[5] Univ Isfahan, Fac Chem, Esfahan 8174673441, Iran
来源：
JOURNAL OF MOLECULAR STRUCTURE | 2013年 / 1054卷
关键词：
Schiff-base; Spectroscopy; Single-crystal; Hydrogen bond; DFT; NICKEL(II) COMPLEXES; CATALYTIC-ACTIVITY; METAL-COMPLEXES; EPOXIDATION; LIGANDS; BONDS;
D O I：
10.1016/j.molstruc.2013.09.026
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
Two new Schiff base compounds 2-{(E)-[2-(bromoethyl)iminolmethyl)-4-bromophenol (1) and 2-{(E)-[2-(chloroethyl)iminolmethyl)-4-bromophenol (2) have been synthesized and characterized by FT-IR and H-1 NMR spectroscopy, elemental analysis, thermal studies and single-crystal X-ray diffraction. They crystallize in the triclinic system, space group P-1. Both Schiff base compounds 1 and 2 display a trans configuration with respect to the C=N double bond. Quantum theory of atoms in molecules (QTAIM) has been also used to find intramolecular interactions and investigate their chemical nature. The results show that in both of the compounds 1 and 2, there is a hydrogen bonding between nitrogen of imine and oxygen of phenol which is considerably stronger than normal hydrogen bonds. In addition, it has been shown that these hydrogen bonds are partially covalent and partially electrostatic in nature, in contrast to normal hydrogen bonds, which are usually considered as electrostatic interactions. (C) 2013 Elsevier B.V. All rights reserved.
引用
收藏
页码：100 / 106
页数：7
相关论文
共 35 条
[11]   VERY STRONG HYDROGEN-BONDING [J].
EMSLEY, J .
CHEMICAL SOCIETY REVIEWS, 1980, 9 (01) :91-124
[12]  
Frisch M., 2004, GAUSSIAN 03 REVISION, DOI DOI 10.1016/J.MOLSTRUC.2017.03.014
[13]   Synthesis, characterization and crystal structure determination of a new oxovanadium(IV) Schiff base complex: The catalytic activity in the epoxidation of cyclooctene [J].
Grivani, Gholamhossein ;
Bruno, Giuseppe ;
Rudbari, Hadi Amiri ;
Khalaji, Aliakbar Dehno ;
Pourteimouri, Pegah .
INORGANIC CHEMISTRY COMMUNICATIONS, 2012, 18 :15-20
[14]   Synthesis, characterization and crystal structures of new bidentate Schiff base ligand and its vanadium(IV) complex: The catalytic activity of vanadyl complex in epoxidation of alkenes [J].
Grivani, Gholamhossein ;
Khalaji, Aliakbar Dehno ;
Tahmasebi, Vida ;
Gotoh, Kazuma ;
Ishida, Hiroyuki .
POLYHEDRON, 2012, 31 (01) :265-271
[15]  
HOBDAY MD, 1973, COORDIN CHEM REV, V9, P311, DOI 10.1016/S0010-8545(00)82081-0
[16]  
Jeffrey G. A., 1997, An Introduction to Hydrogen Bonding
[17]   Synthesis, characterization and crystal structures of nickel complexes with dissymmetric tetradentate ligands containing a mixed-donor sphere [J].
Kaasjager, VE ;
Puglisi, L ;
Bouwman, E ;
Driessen, WL ;
Reedijk, J .
INORGANICA CHIMICA ACTA, 2000, 310 (02) :183-190
[18]   Synthesis and biological activity of Schiff and Mannich bases bearing 2,4-dichloro-5-fluorophenyl moiety [J].
Karthikeyan, Mari Sithambaram ;
Prasad, Dasappa Jagadeesh ;
Poojary, Boja ;
Bhat, K. Subrahmanya ;
Holla, Bantwal Shivarama ;
Kumari, Nalilu Suchetha .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (22) :7482-7489
[19]  
Keith T.A., 2011, AIMAII VERSION 11 02
[20]   Homo- and mixed-valence EPR -active trinuclear manganese complexes [J].
Kessissoglou, DP .
COORDINATION CHEMISTRY REVIEWS, 1999, 185-6 :837-858
1234