Mechanistic, energetic and structural studies of single-walled carbon nanotubes functionalized with penicillamine

Hosein Shaki, Ali Morsali, Heidar Raissi, Mohammad Hakimi, S. Ali Beyramabadi

Abstract


Using density functional theory, the possible noncovalent interactions and six mechanisms of covalent functionalization of drug penicillamine with functionalized carbon nanotube (CNT) have been investigated. Quantum molecular descriptors of noncovalent configurations were studied. It was specified that binding of drug penicillamine with functionalized CNT is thermodynamically suitable. COOH functionalized CNT (NTCOOH) has more binding energy than COCl functionalized CNT (NTCOCl) and can act as a favorable system for penicillamine drug delivery within biological and chemical systems (noncovalent). NTCOOH and NTCOCl can bond to the NH2, OH and SH groups of penicillamine through OH (COOH mechanism) and Cl (COCl mechanism) groups, respectively. The activation energies, the activation enthalpies and the activation Gibbs free energies of six pathways were calculated and compared with each other. The activation parameters related to COOH mechanism are higher than those related to COCl mechanism and therefore COCl mechanism is suitable for covalent functionalization. These results could be generalized to other similar drugs.


Keywords


density functional theory; quantum molecular descriptors; covalent and noncovalent functionalization; reaction mechanisms

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DOI: http://dx.doi.org/10.2298/JSC170218072S

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