Molecular electrostatic potentials. Mechanistic aspects of electrophilic attack on furan

Politzer, Peter; Donnelly, Robert A.; Daiker, Kenneth C.

doi:10.1039/c39730000617

Cited by 20 publications

(7 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Some years ago, we examined the electrostatic potentials of furan, 3 , and pyrrole, 4 , in their molecular planes, and we looked at the effects of moving hydrogens out of these planes 68, 69. Now we present the potentials on the molecular surfaces, in Figure 2, and V S ,min and \documentclass{article}\pagestyle{empty}\begin{document}$\bar{I}_{S,\mathrm{min}}$\end{document}, in Table III.…”

Section: Complementary Roles Of Vs(r) and \Documentclass{article}\pagmentioning

confidence: 99%

The complementary roles of molecular surface electrostatic potentials and average local ionization energies with respect to electrophilic processes

Politzer

Murray

Concha

2002

Int J of Quantum Chemistry

Self Cite

176

View full text Add to dashboard Cite

ABSTRACT:We focus upon two properties, the electrostatic potential V(r) and the average local ionization energyĪ(r). When evaluated on molecular surfaces, V S (r) andĪ S (r) can be useful tools for analyzing and predicting reactive behavior. V S (r) is most reliable with respect to noncovalent interactions; when electrophilic attack and some degree of charge transfer are involved, then the combination of V S (r) andĪ S (r) can be quite effective. They play complementary roles: V S (r) reveals the regions of the molecule to which an electrophile would initially be attracted, andĪ S (r) indicates the ease of charge transfer at these and other sites. Four examples of such complementarity are discussed, involving benzene derivatives, guanine and cytosine, furan and pyrrole, and binary hydrides.

show abstract

Section: Complementary Roles Of Vs(r) and \Documentclass{article}\pagmentioning

confidence: 99%

The complementary roles of molecular surface electrostatic potentials and average local ionization energies with respect to electrophilic processes

Politzer

Murray

Concha

2002

Int J of Quantum Chemistry

Self Cite

176

View full text Add to dashboard Cite

show abstract

“…They employed the positive and negative regions generated by texturing the MESP on a molecular surface for identifying the sites of nucleophilic and electrophilic attack, respectively [ 23 , 36 , 37 , 38 ]. These pioneering studies led to extensive application of MESP to describe chemical properties such as bonding, inductive and resonance effects, and prediction of the protonation sites of organic molecules including nucleic acid bases as well as hydration sites of large molecules [ 29 , 33 , 34 , 39 , 40 ]. MESP has also been useful for exploring molecular recognition in biological systems.…”

Section: Introductionmentioning

confidence: 99%

“…Early works of Scrocco, Tomasi and the Pullmans [29][30][31][32] established MESP as a guiding scalar field for understanding the reactive behavior of molecules. Later, Politzer and co-workers popularized the qualitative use of MESP to predict the molecular sites amenable to electrophilic and nucleophilic attack [23,[33][34][35]. They employed the positive and negative regions generated by texturing the MESP on a molecular surface for identifying the sites of nucleophilic and electrophilic attack, respectively [23,[36][37][38].…”

Section: Introductionmentioning

confidence: 99%

Electrostatic Potential Topology for Probing Molecular Structure, Bonding and Reactivity

2021

View full text Add to dashboard Cite

Following the pioneering investigations of Bader on the topology of molecular electron density, the topology analysis of its sister field viz. molecular electrostatic potential (MESP) was taken up by the authors’ groups. Through these studies, MESP topology emerged as a powerful tool for exploring molecular bonding and reactivity patterns. The MESP topology features are mapped in terms of its critical points (CPs), such as bond critical points (BCPs), while the minima identify electron-rich locations, such as lone pairs and π-bonds. The gradient paths of MESP vividly bring out the atoms-in-molecule picture of neutral molecules and anions. The MESP-based characterization of a molecule in terms of electron-rich and -deficient regions provides a robust prediction about its interaction with other molecules. This leads to a clear picture of molecular aggregation, hydrogen bonding, lone pair–π interactions, π-conjugation, aromaticity and reaction mechanisms. This review summarizes the contributions of the authors’ groups over the last three decades and those of the other active groups towards understanding chemical bonding, molecular recognition, and reactivity through topology analysis of MESP.

show abstract

“…The electrostatic potential field cD(F), generated by the total electronic charge distribution p1 (r) and the nuclei Z, has been found to provide a reliable qualitative description of chemical interactions involving ionic mechanisms [4,[8][9][10] and to represent a valid approximation to the molecular potential in high-energy electron scattering problems [ 111. It was suggested that the pattern of the electrostatic potential generated by the active molecules could be studied as a template for the matching interactions with the receptor that determine the geometries of approach and sites of interaction in the early stages of receptor recognition [6].…”

Section: The Interaction Warmacophorementioning

confidence: 99%

Some new quantum chemical procedures for the analysis of drug-receptor interactions

Weinstein

2009

Int. J. Quantum Chem.

View full text Add to dashboard Cite

The interaction of biologically active molecules with macromolecular receptors is analyzed in terms of preferred intermolecular orientation and the resulting intermolecular forces. The concept of an interaction pharmacophore representing a reactivity index for biologically active molecules and the representation of this pharmacophore by molecular electrostatic potentials are discussed and illustrated. A theoretical method for the analysis o f multiple-site interactions of large molecules is presented in terms of a double perturbation formalism. The method is applied to the model system of adenine interacting simultaneously with a molecule of water and an approaching proton. The results illustrate a possible mechanism for the preferential activation of secondary sites when a large molecule is already interacting at a primary reactive site.

show abstract

Molecular electrostatic potentials. Mechanistic aspects of electrophilic attack on furan

Cited by 20 publications

References 0 publications

The complementary roles of molecular surface electrostatic potentials and average local ionization energies with respect to electrophilic processes

The complementary roles of molecular surface electrostatic potentials and average local ionization energies with respect to electrophilic processes

Electrostatic Potential Topology for Probing Molecular Structure, Bonding and Reactivity

Some new quantum chemical procedures for the analysis of drug-receptor interactions

Contact Info

Product

Resources

About