Abstract
Nitron is the trivial name of (1,4-diphenyl-4H-1,2,4-triazol-3-yl)phenyl-amine (C20H16N4), a triazole derivative used as an analytical reagent for gravimetric analysis of the nitrate anion. The crystal structure of the di-fluoro-phosphate salt of Nitron, 3-anilino-1,4-diphenyl-1H-1,2,4-triazol-4-ium di-fluoro-phosphate, C20H17N4 +·PO2F2 -, is reported here. Within the protonated Nitron mol-ecule, the triazole ring, one of the phenyl rings and the NHPh moiety are virtually co-planar, with the third phenyl ring inclined to the least-squares plane of the other three rings by 56.07 (3)°. Inter-molecular N-H⋯O and C-H⋯O hydrogen bonds between cations and di-fluoro-phosphate anions lead to the formation of a three-dimensional network that is consolidated by additional π-π stacking inter-actions between the triazole ring and one of the phenyl rings. Database surveys on inorganic, metal-organic and organic structures comprising the tetra-hedral PO2F2 group reveal mean bond lengths of P-O = 1.459 (27) Å, P-F = 1.530 (21) Å, and angles of O-P-O = 121.2 (2.9)°, O-P-F = 108.7 (6)°, and F-P-F = 98.5 (2.6)°, using a dataset of 67 independent PO2F2 - anions or PO2F2 entities.
Highlights
Nitron is the trivial name of (1,4-diphenyl-4H-1,2,4-triazol-3-yl)phenylamine (C20H16N4), a triazole derivative used as an analytical reagent for gravimetric analysis of the nitrate anion
Intermolecular N—HÁ Á ÁO and C—HÁ Á ÁO hydrogen bonds between cations and difluorophosphate anions lead to the formation of a three-dimensional network that is consolidated by additional – stacking interactions between the triazole ring and one of the phenyl rings
Nitron is the trivial name for the triazole derivative (1,4diphenyl-4H-1,2,4-triazol-3-yl)phenylamine, C20H16N4, that shows tautomerism and can be present in its zwitterionic form (I) or its NHC-type carbenic form (II) (Fig. 1)
Summary
Nitron is the trivial name for the triazole derivative (1,4diphenyl-4H-1,2,4-triazol-3-yl)phenylamine, C20H16N4, that shows tautomerism and can be present in its zwitterionic form (I) or its NHC-type carbenic form (II) (Fig. 1). Nitron has been utilized as a reagent for gravimetric analysis of the nitrate anion (‘Busch’s reagent’; Busch, 1905) from slightly acidic solutions under formation of the salt C20H17N4+ÁNO3À. The Nitron salt of difluorophosphoric acid, C20H17N4+ÁPO2F2À (III) was reported by Lange more than 90. It can be used as a precursor for obtaining difluorophosphates of several metals or other cations through metathesis reactions. The synthesis, crystallization and structure analysis of III are reported here, together with a survey of the structural characteristics of the difluorophosphate anion present in inorganic, metal–organic and organic compounds. Symmetry code: (i) Àx þ 32; y À 12; Àz þ 12
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