Akademik Veri Yönetim Sistemi
MOLECULAR PHYSICS, cilt.122, sa.10, ss.2279261-2279277, 2024 (SCI-Expanded, Scopus)
Herein, the molecular structures of amide ↔ imide tautomers of articaine (ART) were computation-ally investigated at the DFT/B3LYP/6–311++G (d,p) methodology. Experimental FT-IR and UV-Vischaracterisation results of ART were compared with the theoretical results of amide (ART-A) andimide (ART-I) forms. Thermodynamic parameters computed for each phase revealed that the amidetautomer of ART was preferred with energy values in the range of 11.9–13.8 kcal/mol. The modi-fication in surface properties as a function of prototropic tautomerism in the ART molecule wasstudied by electrostatic surface properties (ESP) analysis. Frontier molecular orbital (FMO), natu-ral bond orbital (NBO), and nonlinear optical (NLO) analyses were performed. It is revealed thatenergy gap values of the ART-I (4.670–4.738 eV) for each phase are slightly higher than those ofthe corresponding phases in the ART-A (4.515–4.586 eV). Therefore, it can be concluded that theimide form exhibits lower chemical reactivity compared to the amide form. Regarding NLO char-acteristics, dipole moment (μtot), mean polarisability (αtot), and mean first-order hyperpolarisability(βtot) values of tautomers have been reported. It was determined that the βtot values computed forART-A (0.653 × 10−30 esu) and ART-I (0.710 × 10−30 esu) were approximately twice the value of thestandard urea.ARTICLE HISTORYReceived 6 October 2023Accepted 31 October 2023KEYWORDSPrototropic tautomerism;Articaine; Reactivity; DFT;NBO analysis1. IntroductionPain is the fear that the patient is afraid to experi-ence during surgical operations and subsequent care.Therefore, pain management is the most importantfactor in this process [1]. Anaesthesia provides apainless application of surgical operations. While thewhole body is affected by general anaesthesia, onlyCONTACT Sümeyya Serin sumeyya.alatas@inonu.edu.tr Scientific and Technological Research Center, Inonu University, 44280 Malatya, TurkeySupplemental data for this article can be accessed online at https://doi.org/10.1080/00268976.2023.2279261.the part to be treated is desensitised to local anaes-thesia. Local anaesthetics, which are widely used espe-cially in dentistry and can be applied alone or togetherwith adjuvants, reversibly interrupt nerve signals. Themolecular structure of local anaesthetics consists of alipophilic aromatic ring, intermediate ester or amidelinkage, and tertiary amine. Cocaine, chloroprocaine,© 2023 Informa UK Limited, trading as Taylor & Francis Group