Journal of Molecular Structure, ( ISI ), Volume (1072), Year (2014-6) , Pages (187-194)

Title : ( Synthesis, characterization and intramolecular proton transfer of 3,3’-Dihydroxy-4,4’-[5-methyl-1,3-phenylenebis(nitrilomethylidyne)]-bis-phenol )

Authors: Hossein Eshtiagh Hosseini , S. Ali Beyramabadi , Ali Morsali , Masoud Mirzaei Shahrabi , Hamed Chegini , Morteza Elahi , Mohammad Ali Naseri ,

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A newly synthesized Schiff base, 3,3’-Dihydroxy-4,4’-[5-methyl-1,3-phenylenebis(nitrilomethylidyne)]-bis-phenol, was characterized experimentally. Its geometries optimization, tautomerization, assignment of the IR bands and NMR chemical shifts were calculated by using density functional theory (DFT) method. In addition, the Atoms in molecules (AIM) analysis was employed for investigation of its tautomerization. Four possible tautomers of the investigated Schiff base were optimized in both of the gas and solution phases. The Schiff base has no planar structure, but each of the benzene rings is in a separate plane. In the most stable tutomer, the phenolic protons of the two –OH groups are engaged in the intramolecular-hydrogen bond with the azomethine nitrogens. Good consistency between the theoretical and experimental results confirms validity of the optimized geomrtry. Also, kinetics and mechanism of the intramolecular-proton transfer of the studied Schiff base was demonstrated theoretically.

Keywords

Schiff Base; DFT; Assignment; Intramolecular Proton Transfer; AIM analysis;
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@article{paperid:1041332,
author = {Eshtiagh Hosseini, Hossein and S. Ali Beyramabadi and Ali Morsali and Mirzaei Shahrabi, Masoud and Hamed Chegini and Morteza Elahi and Mohammad Ali Naseri},
title = {Synthesis, characterization and intramolecular proton transfer of 3,3’-Dihydroxy-4,4’-[5-methyl-1,3-phenylenebis(nitrilomethylidyne)]-bis-phenol},
journal = {Journal of Molecular Structure},
year = {2014},
volume = {1072},
month = {June},
issn = {0022-2860},
pages = {187--194},
numpages = {7},
keywords = {Schiff Base; DFT; Assignment; Intramolecular Proton Transfer; AIM analysis; Tautomerization},
}

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%0 Journal Article
%T Synthesis, characterization and intramolecular proton transfer of 3,3’-Dihydroxy-4,4’-[5-methyl-1,3-phenylenebis(nitrilomethylidyne)]-bis-phenol
%A Eshtiagh Hosseini, Hossein
%A S. Ali Beyramabadi
%A Ali Morsali
%A Mirzaei Shahrabi, Masoud
%A Hamed Chegini
%A Morteza Elahi
%A Mohammad Ali Naseri
%J Journal of Molecular Structure
%@ 0022-2860
%D 2014

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