A Comparative DFT Study of the Chemical Reactivity of Diastereoisomers Cis/trans Clovamides and Derivatives, Isolated from icacina mannii

N’guessan Kan Lucien Yao^1, , Doh Soro², Kouakou Nobel N’Guessan³, Anoubilé Benié¹, Stephane Dembele³, Philomène Akoua Kouassi-Yao² and Nahosse Ziao³

¹Laboratoire de Chimie BioOrganique et de Substances Naturelles, UFR-SFA, Université Nangui Abrogoua, Abidjan, Côte-d’Ivoire

²Université Polytechnique de San Pedro, San Pedro, Côte d'Ivoire

³Laboratoire de Thermodynamique et de Physico-Chimie du Milieu, UFR SFA, Université Nangui Abrogoua, Abidjan, Côte d’Ivoire

Cite this paper:
N’guessan Kan Lucien Yao, Doh Soro, Kouakou Nobel N’Guessan, Anoubilé Benié, Stephane Dembele, Philomène Akoua Kouassi-Yao and Nahosse Ziao. A Comparative DFT Study of the Chemical Reactivity of Diastereoisomers Cis/trans Clovamides and Derivatives, Isolated from icacina mannii. Journal of Materials Physics and Chemistry. 2025; 13(1):8-15. doi: 10.12691/jmpc-13-1-2

Abstract

This study investigates the chemical reactivity of a set of Clovamides and derivatives, including newly identified cis-diastereoisomers, through Density Functional Theory (DFT). Using the B3LYP/6-31+G(d,p) level of theory, global and local reactivity descriptors—such as HOMO-LUMO gap, electronegativity, hardness, electrophilicity, and Fukui functions—were calculated to evaluate reactivity profiles. Clovamide (Clova02) emerged as the most reactive compound due to its low energy gap and hardness, while Clova01 showed the highest electrophilic character. Local reactivity analysis identified O26 and O24 as the most nucleophilic, and C11 and C1 as the most electrophilic centers. Additionally, C20 and C23 on the phenylalanine moiety were revealed as sites favorable to radical attack. The study highlights the comparable reactivity of the newly isolated cis-Clovamide isomers to their trans counterparts, supporting further interest in their synthesis and potential biological applications.

Keywords:
Clovamides and derivatives DFT Diastereoisomers Antioxidant Fukui Indices

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