| Authors | ,,,, |
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| Journal | Journal of Molecular Structure-theochem |
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| Page number | 1-9 |
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| Serial number | 960 |
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| Volume number | 960 |
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| Paper Type | Full Paper |
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| Published At | 2010 |
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| Journal Type | Typographic |
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| Journal Country | Netherlands |
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| Journal Index | ISI،JCR |
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| Keywords | 3, mercapto, propenethial Resonance, assisted hydrogen bonds (RAHB) Related rotamers method DFT calculations AIM NBO Harmonic oscillator model of aromaticity index (HOMA) |
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Abstract
We are presenting a density functional calculation utilizing Beck three parameters hybrid, correlation
functional of Lee, Yang and Parr (B3LYP), MP2 and G2MP2 levels of theory to probe the influence of
R1, R2 and R3 substitutions on 3-mercapto-propenethial, estimating (i) The p-electron delocalization
parameter (Q) as a geometrical indicator of a local aromaticity, (ii) the geometry-based HOMA index
and (iii) intramolecular hydrogen-bond strength. The effects of F, H, Cl, CH3, OH, and NH2 as substituents
are examined. Furthermore the topological properties of the electron density distributions for S–
Hintramolecular bridges are analyzed in terms of the Bader theory of atoms in molecules (AIM). The
electron density (q) and Laplacian (r2
q) properties, estimated by AIM calculations, indicate that SH
bond possesses low q and positive r2
q values which are in agreement with electrostatic character of
the HBs, whereas S–H bonds have covalent character (r2
q < 0). Natural population analysis data, the
electron density and Laplacian properties, as well as, t(S–H) and c(S–H) have been used to evaluate the
hydrogen bonding interactions.
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