Two derivatives of 1,5-disubstituted tetrazoles: 1-(4-nitrophenyl)-1H-tetrazol-5-amine and {(E)-[1-(4-ethoxyphenyl)-1H-tetrazol-5-yl]iminomethyl}dimethylamine.
The geometric features of 1-(4-nitrophenyl)-1H-tetrazol-5-amine, C(7)H(6)N(6)O(2), correspond to the presence of the essential interaction of the 5-amino group lone pair with the pi system of the tetrazole ring. Intermolecular N-H...N and N-H...O hydrogen bonds result in the formation of infinite chains running along the [110] direction and involve centrosymmetric ring structures with motifs R(2)(2)(8) and R(2)(2)(20). Molecules of {(E)-[1-(4-ethoxyphenyl)-1H-tetrazol-5-yl]iminomethyl}dimethylamine, C(12)H(16)N(6)O, are essentially flattened, which facilitates the formation of a conjugated system spanning the whole molecule. Conjugation in the azomethine N=C-N fragment results in practically the same length for the formal double and single bonds.
Lyakhov
Alexander S
AS
Research Institute for Physico-Chemical Problems, Belarusian State University, Leningradskaya Street 14, Minsk 220030, Belarus. lyakhov@bsu.by
Vorobiov
Andrey N
AN
Ivashkevich
Ludmila S
LS
Gaponik
Pavel N
PN
D000588:Amines / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008744:Methylamines / Q000737:chemistry*; D008745:Methylation; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D013777:Tetrazoles / Q000737:chemistry*
C533717:((E)-(1-(4-ethoxyphenyl)-1H-tetrazol-5-yl)iminomethyl)dimethylamine; C533716:1-(4-nitrophenyl)-1H-tetrazol-5-amine; D000588:Amines; D008744:Methylamines; D013777:Tetrazoles