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What roles do boron substitutions play in structural, tautomeric, base pairing and electronic properties of uracil? NBO & AIM analysis

AliakbarTehrani, Z ; Sharif University of Technology | 2012

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  1. Type of Document: Article
  2. DOI: 10.1002/poc.2918
  3. Publisher: Wiley , 2012
  4. Abstract:
  5. The synthesis of modified versions of deoxyribonucleic acid is an area that is receiving much attention. The replacement of the nitrogen atom on the nucleobases with boron atom has provided insight into deoxyribonucleic acid and ribonucleic acid stability, recognition, and replication at the atomic level. In the present research, we investigated a detailed density functional theory study of the structural, tautomeric, base-pairing ability, bond dissociation energy, and electronic properties of two boron analogues (i.e., boron substitutions at 4-position and 5-position of uracil) of uracil nucleobase. The effects of these modifications on theirs acid-base properties have been considered. Our goal is to gather data to help elucidate the structure and electronic properties of boron analogues of uracil. Density functional theory calculations were performed using a nonlocal hybrid B3LYP and 6-311++G (d,p) atomic basis set. The result of calculation revealed that the canonical 'keto' form is the most stable tautomeric form of uracil nucleobase and its boronated analogues in the gas phase at density functional theory and second-order Møller-Plesset levels. Hyperconjugation stabilization factors that affect the stability of generated radicals and anions in these molecules were investigated by natural bond orbital analysis. Furthermore, quantum theory of atoms in molecules analysis was performed to extract the bond critical point properties of various base pairs. The electron density can be considered as a good description of the strength of the different types of hydrogen bonding
  6. Keywords:
  7. Base pair ; Density functional theory study ; Hydrogen bonding ; Tautomers ; Acid-base property ; AIM analysis ; Atomic basis set ; Atomic levels ; Atoms in molecules theory ; Base pairs ; Base-pairing ; Bond critical points ; Bond dissociation energies ; Boron atom ; Density functional theory calculations ; Gasphase ; Hyperconjugation ; Natural bond orbital analysis ; Nitrogen atom ; Nonlocal ; Nucleobases ; Quantum Theory of Atoms in Molecules ; Second orders ; Stabilization factors ; Tautomeric forms ; Aromatic compounds ; Atoms ; Boron ; Carrier concentration ; DNA ; Electronic properties ; Factor analysis ; Hydrogen bonds ; Organic acids ; Quantum theory ; RNA ; Stabilization ; Density functional theory
  8. Source: Journal of Physical Organic Chemistry ; Volume 25, Issue 9 , 2012 , Pages 787-796 ; 08943230 (ISSN)
  9. URL: http://onlinelibrary.wiley.com/doi/10.1002/poc.2918/full