A theoretical prediction of stability in hydrogen-bonded complexes formed between oxirane and oxetane rings with HX (X=F and Cl).
The optimised geometries of heterocyclic hydrogen-bonded complexes, C2H4O...HX and C3H6O...HX, where X=F or Cl, were determined at DFT/B3LYP/6-311++G(d,p) computational level. Structural, electronic and vibrational properties of these complexes are used in order to compare the strained ring, which confer the great reactivity of these heterocyclic rings with monoprotic acids, forming a primary hydrogen bond. A secondary hydrogen bond between the hydrogen atoms of the CH2 groups and the halide species also takes place, thus causing a nonlinearity (characterized by the theta angle), in the primary hydrogen bond.
Departamento de Ciências Farmacêuticas, Universidade Federal da Paraíba, 58036-300 João Pessoa, PB, Brazil.
F C
FC
Ferreira
B G
BG
Oliveira
E
E
Ventura
S A
SA
do Monte
C F
CF
Braga
R C M U
RC
Araújo
M N
MN
Ramos
D004988:Ethers, Cyclic / Q000737:chemistry; D005027:Ethylene Oxide / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006851:Hydrochloric Acid / Q000737:chemistry*; D006858:Hydrofluoric Acid / Q000737:chemistry*; D006860:Hydrogen Bonding; D008956:Models, Chemical; D008968:Molecular Conformation
D004988:Ethers, Cyclic; D006571:Heterocyclic Compounds; C005287:oxetane; D005027:Ethylene Oxide; D006851:Hydrochloric Acid; D006858:Hydrofluoric Acid