Origin of the high basicity of 2,7-dimethoxy-1,8-bis(dimethylamino)naphthalene: implications for enzyme catalysis

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DOIResolve DOI: http://doi.org/10.1016/S0166-1280(01)00463-8
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TypeArticle
Journal titleJournal of Molecular Structure
Volume547
Issue1-3
Pages113118; # of pages: 6
SubjectBasicity; Density functional theory; Enzymatic catalysis; Hydrogen bond; Proton affinity (PA); Proton sponges; Steric repulsions
AbstractDensity functional calculations on model systems are performed to understand the origin of the large increase of basicity from 1,8-bis(dimethylamino)naphthalene (1) to 2,7-dimethoxy-1,8-bis(dimethylamino)naphthalene (2). It is found that the increase of the gas-phase proton affinity (PA) on going from 1 to 2 mainly comes from the relief of steric repulsions of the methoxy groups with their neighboring amino groups as a result of protonation. It is suggested that this relief of the steric repulsions along with favorable electrostatic interactions involving the methoxy groups in 2H+ makes a major contribution to the enhanced basicity.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada; NRC Steacie Institute for Molecular Sciences
Peer reviewedNo
NPARC number12338425
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Record identifierb2145039-f45a-4171-a03d-daee70a2abba
Record created2009-09-10
Record modified2016-05-09
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