The crystal and molecular structure of 5-amino-4-ethoxycarbonyl-1H-1,2,3-triazole, C₅H₈N₄O₂

Abstract

CsHaN402 is monoclinic, space group P2~/c, with a = 10.667 (2), b = 6.287 (2), c = 10.881 (2) ,~,/3 = 94.39 (10) °, Z = 4. The structure was refined to R = 0.085 for 1281 observed reflexions. The tautomerism of the 1,2,3-triazoles can be characterized by the bond angles in the five-membered rings. The hydrogen bonding formed in the presence of the ethoxycarbonyl group is compared with that in related compounds.

Basicity of N-H- and N-Methyl-1,2,3-triazoles in the Gas Phase, in Solution, and in the Solid State − An Experimental and Theoretical Study

“…The hydrogen atoms were located unambiguously, the bond length and angle patterns (Table 5 and Figure 3) shown by the triazole rings are different and, the substituent aside, both patterns are consistent with the nondisordered structures reported for the corresponding tautomers (CSD [47] ref. codes for 1H tautomers: AEXTAZ, [48] ATZCBX; [49] 2H tautomers: COMLEV, [50] MSACTZ10, [51] and RUVQOO [46] ). The bond angles in both compounds reflect the electronic properties of the phenyl and nitro substituents, [52] which close and open the endocyclic angle at C4 and break the C 2v symmetry of the ring.…”

Synthesis, Characterization, and Structural Investigations of 1‐Amino‐3‐substituted‐1,2,3‐triazolium Salts, and a New Route to 1‐Substituted‐1,2,3‐triazoles.

“…Due to its high biological activity, substituted 1,2,3-triazoles have been studied extensively by single crystal X-ray diffraction. To date, all these studies focus on substituted and annulated compounds [40][41][42][43][44][45][46][47][48][49][50][51][52][53][54][55][56]. However there are no reports discussing the crystal structures of any unsubstituted 1-amino-1,2,3-triazoles.…”

“…7 substituted and annulated compounds [40][41][42][43][44][45][46][47][48][49][50][51][52][53][54][55][56]. However there are no reports discussing the crystal structures of any unsubstituted 1-amino-1,2,3-triazoles.…”

The crystal and molecular structure of 2-methyl-5-[methyl(mesyl)amino]-2H-1,2,3-triazole-4-carbonitrile. On the geometry of the N-mesyl groups

“…5-amino-4-carbamoyl-lH-1,2,3-triazole (Kalmhn, Simon, Schawartz & Horv~th, 1974), tetrachlorobis[2-(5-amino-4-carboxamidinium)-1H-1,2,3-triazole]-copper monohydrate (Purnell,Shepherd & Hodgson,19 75) and 5-amino-4-ethoxycarbonyl-1 H-1,2,3-triazole (P~rk~nyi, K~tlm~.n, Argay & Schawartz, 1977)}. In order to obtain a better view of this unusual 2H-tautomerism of (I), X-ray analysis of its dimethyl derivative (II) was performed.…”