Chemistry of Heterocyclic Compounds, Vol. 43, No. 3, 2007
SYNTHESIS AND STRUCTURE OF TRIS(5-PHENYLTETRAZOL-1-YL)METHANE
R. E. Trifonov
1
, G. V. Gurskaya
2
, A. V. Gaenko
3
,
V. E. Zavodnik
4
, and V. A. Ostrovskii
1
The interaction of 5-phenyltetrazolate anion with chloroform in strongly alkaline medium leads to the
formation of tris(5-phenyltetrazol-1-yl)methane and 2-dichloromethyl-5-phenyltetrazole. The structures
of tris(5-phenyltetrazol-1-yl)-methane and of its isomer tris(5-phenyltetrazol-2-yl)methane have been
investigated by X-ray structural analysis and theoretical calculations carried out on the B3LYP/6-
31G** basis.
Keywords: polynuclear heterocycles, tetrazole, X-ray structural analysis, theoretical calculations by the
DFT method.
Polynuclear tetrazoles are considered as efficient ligands for binding metal ions [1, 2], and also as
potentially biologically active substances [3]. Information on polytetrazolylmethanes is limited in comparison
with other poly-N-azolylalkanes. We previously reported the synthesis of one such compound [4]. In the present
work we have investigated the reaction of 5-phenyltetrazolate anion with chloroform under various conditions
(aqueous NaOH solutions of various concentration, in the presence or absence of a phase-transfer catalyst) and
also the structures of the compounds obtained.
N
N
N
N
Ph H
N
N
N
N
Ph
NaOH
N
N
N
N
Ph
CHCl
2
N
N
N
N
Ph
CH
N
Ph
N
N
CH
N
CHCl
3
CHCl
3
–
3
1
2
3
5
4
3
In alkaline medium 5-phenyltetrazole 1 dissociates with the formation of the corresponding anion 2, the
reaction of which with chloroform leads to 2-dichloromethyl-5phenyltetrazole (3) and tris(5-phenyltetrazol-1-
yl)methane (4). The presence of tris(5-phenyltetrazol-2-yl)methane (5) in the reaction products was not
__________________________________________________________________________________________
1
Saint Petersburg State Technological Institute (Technical University), Saint Petersburg 190013, Russia;
e-mail: va_ostrovskii@mail.ru.
2
V. A. Engelgardt Institute of Molecular Biology, Russian Academy of Sciences,
Moscow 119991; e-mail: gurskayia@eimb.ru.
3
Department of Theoretical Chemistry, Chemical Center, Lund
University, Lund, S-221 00, Sweden; e-mail: galev@inbox.ru.
3
L. Ya. Karpov Research Institute for Physical
Chemistry, Moscow 105064, Russia. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 398-
404, March, 2007. Original article submitted August 3, 2006.
320 0009-3122/07/4303-0320©2007 Springer Science+Business Media, Inc.