| DOI | Resolve DOI: https://doi.org/10.1016/S0166-1280(01)00463-8 |
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| Author | Search for: Guo, Hong; Search for: Salahub, Dennis R.1 |
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| Affiliation | - National Research Council of Canada. NRC Steacie Institute for Molecular Sciences
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| Format | Text, Article |
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| Subject | Basicity; Density functional theory; Enzymatic catalysis; Hydrogen bond; Proton affinity (PA); Proton sponges; Steric repulsions |
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| Abstract | Density 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. |
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| Publication date | 2001-07-23 |
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| In | |
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| Language | English |
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| NPARC number | 12338425 |
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| Export citation | Export as RIS |
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| Report a correction | Report a correction (opens in a new tab) |
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| Record identifier | b2145039-f45a-4171-a03d-daee70a2abba |
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| Record created | 2009-09-10 |
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| Record modified | 2020-03-27 |
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