Vibrational (FT-IR), electronic (UV-Vis), thermodynamic, and NBO analyses of amide ? imide forms of articaine: a computational perspective on prototropic tautomerism

Küçük Resim Yok

Tarih

2024

Dergi Başlığı

Dergi ISSN

Cilt Başlığı

Yayıncı

Taylor & Francis Ltd

Erişim Hakkı

info:eu-repo/semantics/closedAccess

Özet

Herein, the molecular structures of amide <-> imide tautomers of articaine (ART) were computationally investigated at the DFT/B3LYP/6-311++G (d,p) methodology. Experimental FT-IR and UV-Vis characterisation results of ART were compared with the theoretical results of amide (ART-A) and imide (ART-I) forms. Thermodynamic parameters computed for each phase revealed that the amide tautomer of ART was preferred with energy values in the range of 11.9-13.8 kcal/mol. The modification in surface properties as a function of prototropic tautomerism in the ART molecule was studied by electrostatic surface properties (ESP) analysis. Frontier molecular orbital (FMO), natural bond orbital (NBO), and nonlinear optical (NLO) analyses were performed. It is revealed that energy gap values of the ART-I (4.670-4.738 eV) for each phase are slightly higher than those of the corresponding phases in the ART-A (4.515-4.586 eV). Therefore, it can be concluded that the imide form exhibits lower chemical reactivity compared to the amide form. Regarding NLO characteristics, dipole moment (mu(tot)), mean polarisability (alpha(tot)), and mean first-order hyperpolarisability (beta(tot)) values of tautomers have been reported. It was determined that the beta(tot) values computed for ART-A (0.653 x 10(-30) esu) and ART-I (0.710 x 10(-30) esu) were approximately twice the value of the standard urea. [GRAPHICS]

Açıklama

Anahtar Kelimeler

Prototropic tautomerism, Articaine, Reactivity, DFT, NBO analysis

Kaynak

Molecular Physics

WoS Q Değeri

Q3

Scopus Q Değeri

Q3

Cilt

122

Sayı

10

Künye