Molecular Orbital (CNDO/2 and MINDO) Calculations on Protonated Deoxyribonucleic Acid Bases. The Effects of Base Protonation on Intermolecular Interactions

Frank Jordan; Henry Dirk Sostman

doi:10.1021/ja00801a004

Molecular Orbital (CNDO/2 and MINDO) Calculations on Protonated Deoxyribonucleic Acid Bases. The Effects of Base Protonation on Intermolecular Interactions

Frank Jordan, Henry Dirk Sostman

Research output: Contribution to journal › Article › peer-review

41 Scopus citations

Abstract

The electronic reorganization accompanying monoprotonation of DNA bases was examined employing all-valence-electron SCF molecular orbital methods, σ as well as π reorganization upon protonation is evident in all four bases. Stacking and hydrogen-bonding interactions were calculated including monopole-monopole, monopole-induced dipole, and dispersion terms between the various bases in their neutral and monoprotonated states for all possible combinations. The intermolecular interactions are invariably move favorable for half-protonated pairs (i.e., one base protonated) than for neutral pairs. Stacking interactions are always unfavorable in doubly protonated pairs (i.e., both bases protonated).

Original language	English (US)
Pages (from-to)	6544-6554
Number of pages	11
Journal	Journal of the American Chemical Society
Volume	95
Issue number	20
DOIs	https://doi.org/10.1021/ja00801a004
State	Published - Oct 1 1973

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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abstract = "The electronic reorganization accompanying monoprotonation of DNA bases was examined employing all-valence-electron SCF molecular orbital methods, σ as well as π reorganization upon protonation is evident in all four bases. Stacking and hydrogen-bonding interactions were calculated including monopole-monopole, monopole-induced dipole, and dispersion terms between the various bases in their neutral and monoprotonated states for all possible combinations. The intermolecular interactions are invariably move favorable for half-protonated pairs (i.e., one base protonated) than for neutral pairs. Stacking interactions are always unfavorable in doubly protonated pairs (i.e., both bases protonated).",

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Y1 - 1973/10/1

N2 - The electronic reorganization accompanying monoprotonation of DNA bases was examined employing all-valence-electron SCF molecular orbital methods, σ as well as π reorganization upon protonation is evident in all four bases. Stacking and hydrogen-bonding interactions were calculated including monopole-monopole, monopole-induced dipole, and dispersion terms between the various bases in their neutral and monoprotonated states for all possible combinations. The intermolecular interactions are invariably move favorable for half-protonated pairs (i.e., one base protonated) than for neutral pairs. Stacking interactions are always unfavorable in doubly protonated pairs (i.e., both bases protonated).

AB - The electronic reorganization accompanying monoprotonation of DNA bases was examined employing all-valence-electron SCF molecular orbital methods, σ as well as π reorganization upon protonation is evident in all four bases. Stacking and hydrogen-bonding interactions were calculated including monopole-monopole, monopole-induced dipole, and dispersion terms between the various bases in their neutral and monoprotonated states for all possible combinations. The intermolecular interactions are invariably move favorable for half-protonated pairs (i.e., one base protonated) than for neutral pairs. Stacking interactions are always unfavorable in doubly protonated pairs (i.e., both bases protonated).

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Molecular Orbital (CNDO/2 and MINDO) Calculations on Protonated Deoxyribonucleic Acid Bases. The Effects of Base Protonation on Intermolecular Interactions

Abstract

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