Regioselectivity and physical nature of the interactions between (methyl)guanine with HCl and CH3OH
Auteur(s): Diyavanga DetilaNom de la revue/Journal: Discover Chemistry
Volume: 1
Numéro: 1
Année: 2024
pages: 10
Résumé
<p><span style="background-color:rgb(255,255,255);color:rgb(34,34,34);">A comprehensive study of the hydrogen bonding interactions between guanine (</span><strong>G</strong><span style="background-color:rgb(255,255,255);color:rgb(34,34,34);">) and methyl guanine derivatives (</span><strong>MGs</strong><span style="background-color:rgb(255,255,255);color:rgb(34,34,34);">) in the presence of HCl and MeOH is carried out at B3LYP, B3LYP-D3 and M062X/6–311 + + G(d.p) levels using molecular electrostatic potential, natural bond orbital, and symmetry adapted perturbation theory. Making use of these state-of-the-art techniques, this study attempts to elucidate the chemical bonding, regioselectivity, and physical nature of the interactions responsible for the stability of (M)G…L (L = HCl, MeOH) acid–base complexes. Our calculations reveal that </span><strong>1-G</strong><span style="background-color:rgb(255,255,255);color:rgb(34,34,34);">, </span><strong>3-MG</strong><span style="background-color:rgb(255,255,255);color:rgb(34,34,34);">, and </span><strong>5-MG</strong><span style="background-color:rgb(255,255,255);color:rgb(34,34,34);"> interact more strongly with MeOH than HCl due to the positive hydrogen bond cooperativity. Furthermore, the carbonyl site on </span><strong>G</strong><span style="background-color:rgb(255,255,255);color:rgb(34,34,34);"> is found to be the most reactive site, while methyl substitution increases the basicity of the nucleobase, thus yieding more stable complexes. The strongest H-bond </span></p>