Journal of Molecular Structure THEOCHEM

, volume 822 , issue 1-3 , pages 33-37

Relation between the substituent effect and aromaticity in tetrazoles, protonated tetrazoles and tetrazolate derivatives

Alireza Najafi Chermahini ¹

Hossein A Dabbagh ²

Abbas Teimouri ³

Hide authors affiliations Show authors affiliations: 3 affiliations

Department of Chemistry, Faculty of Science, Yasouj university, Yasouj, Iran |

Department of Chemistry, Isfahan University of Technology, Isfahan, Iran. |

Payame Noor University, Isfahan, Iran

Payame Noor University

University of Isfahan

Publication type: Journal Article

Publication date: 2007-11-01

Elsevier

Journal of Molecular Structure THEOCHEM

SJR: —

CiteScore: —

Impact factor: —

ISSN: 01661280

DOI: 10.1016/j.theochem.2007.07.012

Copy DOI

Biochemistry

Physical and Theoretical Chemistry

Condensed Matter Physics

Abstract

The energies, geometries and aromaticity of a series of 5R tetrazoles [R = NH 2 , OH, OCH 3 , SCH 3 , H, CH 3 , F, Cl, BH 2 , CF 3 , CN, NO, NO 2 ], their anions and protonated forms in the gas phase have been calculated with the DFT/B3LYP method at the 6-31++G ∗∗ level. We have analyzed the change of local aromaticity by NICS and HOMA and found a considerable ring aromaticity by tetrazole and tetrazolate anions and their protonated forms. In analysis by NICS, anion forms have the least aromaticity and in neutral forms 1-H tetrazoles have less aromaticity character than 2-H ones. Interestingly among of protonated forms 2,3-H forms have the most aromaticity character and others follow: 1,2-H > 1,3-H > 1,4-H. However, analysis by HOMA index showed that aromaticity is related to nature of groups at the 5 position. The protonated form of 1,4-H tetrazoles have the least aromaticity character.

Found

Top-30

Journals

	1 2
Structural Chemistry	Structural Chemistry, 2, 11.11% Structural Chemistry 2 publications, 11.11%
Journal of Molecular Modeling	Journal of Molecular Modeling, 2, 11.11% Journal of Molecular Modeling 2 publications, 11.11%
Journal of Molecular Structure THEOCHEM	Journal of Molecular Structure THEOCHEM, 2, 11.11% Journal of Molecular Structure THEOCHEM 2 publications, 11.11%
ACS Omega	ACS Omega, 1, 5.56% ACS Omega 1 publication, 5.56%
Chemistry of Heterocyclic Compounds	Chemistry of Heterocyclic Compounds, 1, 5.56% Chemistry of Heterocyclic Compounds 1 publication, 5.56%
Journal of Chemical Sciences	Journal of Chemical Sciences, 1, 5.56% Journal of Chemical Sciences 1 publication, 5.56%
Tetrahedron	Tetrahedron, 1, 5.56% Tetrahedron 1 publication, 5.56%
Computational and Theoretical Chemistry	Computational and Theoretical Chemistry, 1, 5.56% Computational and Theoretical Chemistry 1 publication, 5.56%
Magnetic Resonance in Chemistry	Magnetic Resonance in Chemistry, 1, 5.56% Magnetic Resonance in Chemistry 1 publication, 5.56%
Propellants, Explosives, Pyrotechnics	Propellants, Explosives, Pyrotechnics, 1, 5.56% Propellants, Explosives, Pyrotechnics 1 publication, 5.56%
Chemical Reviews	Chemical Reviews, 1, 5.56% Chemical Reviews 1 publication, 5.56%
RSC Advances	RSC Advances, 1, 5.56% RSC Advances 1 publication, 5.56%
Advances in Heterocyclic Chemistry	Advances in Heterocyclic Chemistry, 1, 5.56% Advances in Heterocyclic Chemistry 1 publication, 5.56%
Canadian Journal of Chemistry	Canadian Journal of Chemistry, 1, 5.56% Canadian Journal of Chemistry 1 publication, 5.56%
	1 2

Publishers

	1 2 3 4 5 6
Springer Nature	Springer Nature, 6, 33.33% Springer Nature 6 publications, 33.33%
Elsevier	Elsevier, 5, 27.78% Elsevier 5 publications, 27.78%
American Chemical Society (ACS)	American Chemical Society (ACS), 2, 11.11% American Chemical Society (ACS) 2 publications, 11.11%
Wiley	Wiley, 2, 11.11% Wiley 2 publications, 11.11%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 1, 5.56% Royal Society of Chemistry (RSC) 1 publication, 5.56%
Canadian Science Publishing	Canadian Science Publishing, 1, 5.56% Canadian Science Publishing 1 publication, 5.56%
	1 2 3 4 5 6

We do not take into account publications without a DOI.
Statistics recalculated weekly.

Are you a researcher?

Create a profile to get free access to personal recommendations for colleagues and new articles.

Metrics

Cite this

GOST |

Cite this

GOST Copy

Najafi Chermahini A., Dabbagh H. A., Teimouri A. Relation between the substituent effect and aromaticity in tetrazoles, protonated tetrazoles and tetrazolate derivatives // Journal of Molecular Structure THEOCHEM. 2007. Vol. 822. No. 1-3. pp. 33-37.

GOST all authors (up to 50) Copy

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1016/j.theochem.2007.07.012

UR - https://doi.org/10.1016/j.theochem.2007.07.012

TI - Relation between the substituent effect and aromaticity in tetrazoles, protonated tetrazoles and tetrazolate derivatives

T2 - Journal of Molecular Structure THEOCHEM

AU - Najafi Chermahini, Alireza

AU - Dabbagh, Hossein A

AU - Teimouri, Abbas

PY - 2007

DA - 2007/11/01

PB - Elsevier

SP - 33-37

IS - 1-3

VL - 822

SN - 0166-1280

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2007_Najafi Chermahini,

author = {Alireza Najafi Chermahini and Hossein A Dabbagh and Abbas Teimouri},

title = {Relation between the substituent effect and aromaticity in tetrazoles, protonated tetrazoles and tetrazolate derivatives},

journal = {Journal of Molecular Structure THEOCHEM},

year = {2007},

volume = {822},

publisher = {Elsevier},

month = {nov},

url = {https://doi.org/10.1016/j.theochem.2007.07.012},

number = {1-3},

pages = {33--37},

doi = {10.1016/j.theochem.2007.07.012}

}

MLA

Cite this

MLA Copy

Najafi Chermahini, Alireza, et al. “Relation between the substituent effect and aromaticity in tetrazoles, protonated tetrazoles and tetrazolate derivatives.” Journal of Molecular Structure THEOCHEM, vol. 822, no. 1-3, Nov. 2007, pp. 33-37. https://doi.org/10.1016/j.theochem.2007.07.012.

Publisher

Elsevier

Journal

Journal of Molecular Structure THEOCHEM

SJR

—

CiteScore

—

Impact factor

—

ISSN

01661280 (Print)