Aliphatic C-H/pi interactions: Methane-benzene, methane-phenol, and methane-indole complexes.
Noncovalent C-H/pi interactions are prevalent in biochemistry and are important in molecular recognition. In this work, we present potential energy curves for methane-benzene, methane-phenol, and methane-indole complexes as prototypes for interactions between C-H bonds and the aromatic components of phenylalanine, tyrosine, and tryptophan. Second-order perturbation theory (MP2) is used in conjunction with the aug-cc-pVDZ and aug-cc-pVTZ basis sets to determine the counterpoise-corrected interaction energy for selected complex configurations. Using corrections for higher-order electron correlation determined with coupled-cluster theory through perturbative triples [CCSD(T)] in the aug-cc-pVDZ basis set, we estimate, through an additive approximation, results at the very accurate CCSD(T)/aug-cc-pVTZ level of theory. Symmetry-adapted perturbation theory (SAPT) is employed to determine the physically significant components of the total interaction energy for each complex.
Ringer
Ashley L
AL
Center for Computational Molecular Science and Technology, School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia 30332-0400, USA.
Figgs
Michelle S
MS
Sinnokrot
Mutasem O
MO
Sherrill
C David
CD
D001554:Benzene / Q000737:chemistry* / Q000378:metabolism; D007211:Indoles / Q000737:chemistry* / Q000378:metabolism; D008697:Methane / Q000737:chemistry* / Q000378:metabolism; D015394:Molecular Structure; D019800:Phenol / Q000737:chemistry* / Q000378:metabolism; D010649:Phenylalanine / Q000737:chemistry; D013816:Thermodynamics; D014364:Tryptophan / Q000737:chemistry; D014443:Tyrosine / Q000737:chemistry
D007211:Indoles; D019800:Phenol; D014443:Tyrosine; D010649:Phenylalanine; D014364:Tryptophan; D001554:Benzene; D008697:Methane