A new treatment of chemical reactivity: Development of EROS, an expert system for reaction prediction and synthesis design

Gasteiger, Johann; Hutchings, Michael G.; Christoph, Bernd; Gann, L.; Hiller, Christian; Löw, Peter; Marsili, Mario; Saller, H.; Yuki, Kazumi

doi:10.1007/3-540-16904-0_14

Cited by 105 publications

(52 citation statements)

References 57 publications

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“…The PEOE method was developed to assign partial atomic charges to sigma-and pi-bonded networks in the course of the development of decision strategies (i.e., prediction of bond reactivities) for the EROS synthetic design program. 23 PEOE charges have been successfully correlated with C-1s ESCA, proton and 13C NMR s h i f t~. '~,~~ The method has also been used to correlate proton sigma charges with proton geminal coupling constants of ethylenesZza and to predict proton affinitiesz5 and dipole moments.…”

Section: Introductionmentioning

confidence: 99%

Electrostatic interactions in molecular mechanics (MM2) calculations via PEOE partial charges I. Haloalkanes

1988

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The PEOE (partial equalization of orbital electronegativity) procedure has been modified slightly and reparametrized for haloalkanes to calculate partial atomic charges suitable for evaluation of dipole moments and electrostatic energies in conjunction with molecular mechanics (MM2) calculations. Dipole moments of 66 haloalkanes are calculated with an average absolute deviation of 0.14 D from experimental values. The conformational energies of 40 compounds have been calculated and the agreement with experimental data is generally good and compares well with calculations by the IDME (induced dipole moment and energy) method. In addition, carbon and proton charges correlate well with C-1s core binding energies and 'H-NMR (nuclear magnetic resonance) shifts for halomethanes. The most striking benefit of treating electrostatics through a set of partial charges compared to the standard MM2 bond dipole approach is demonstrated by calculations on 1,4-disubstituted cyclohexanes, for which standard MM2 fails to predict the most stable conformation.

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Section: Introductionmentioning

confidence: 99%

Electrostatic interactions in molecular mechanics (MM2) calculations via PEOE partial charges I. Haloalkanes

1988

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“…This means that the core problem of synthesis tree pruning is addressed by empirical rules. 88 Similarly, a theoretical approach for the transform/reaction analysis is mounted in the SYNGEN program by Hendrickson, who developed his own system based on symbolic representation of bond formation. 77 SYNCHEM is an example of heuristic programs operated in noninteractive mode.…”

Section: Computer-assisted Synthesis Designmentioning

confidence: 99%

Chemoinformatics

Polański

2009

Comprehensive Chemometrics

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“…The concept of electronegativityl-lo is important in understanding fundamental chemical concepts,", l2 devising reactivity indices, 13 and developing methods for calculating atomic charges14-" in large molecules of biological interest.…”

Section: Introductionmentioning

confidence: 99%

Orbital electronegativity and analytical representation of atom valence state energy

1989

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An analytical representation of atom valence state energy (E(n, ), j = 1,. . .4; E(n,) is a nonlinear function of orbital occupancy numbers n,) is proposed and explicitly derived for H-Ar; the values of electronegativity calculated based on E(n,) agree within truncation error with those of Hinze and Jaffe.However, in our representation, orbital electronegativity x and hardness parameters r) of a given orbital always include nonlinear contributions from other orbitals, hence accounting for their influence on x and r). An atomic charge calculation procedure based on E(n,) is also described and shown to perform well.

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A new treatment of chemical reactivity: Development of EROS, an expert system for reaction prediction and synthesis design

Cited by 105 publications

References 57 publications

Electrostatic interactions in molecular mechanics (MM2) calculations via PEOE partial charges I. Haloalkanes

Electrostatic interactions in molecular mechanics (MM2) calculations via PEOE partial charges I. Haloalkanes

Chemoinformatics

Orbital electronegativity and analytical representation of atom valence state energy

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