Conformational analysis of some phenethylamine molecules

Weintraub, Herschel J. R.; Hopfinger, A. J.

doi:10.1016/0022-5193(73)90189-6

Cited by 39 publications

(10 citation statements)

References 22 publications

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“…(1) and (2) regardless of the region of the sphere involved in the intersection. This resulted in an overestimation of the solvation effect such that all trans, anti-periplanar conformations were proposed for most ionic aryl alkylamines [2].…”

Section: Solvent Modelmentioning

confidence: 99%

“…The details of this calculation are discussed elsewhere [2,3,. The problem of determining the volume of intersection of a sphere with a cylindrical section is not trivial.(!)…”

Section: Solvent Modelmentioning

confidence: 99%

“…The CAMSEQ software system [ 11, in particular, has been used in the study of a large number of congeneric series including phenethylamines [2], tryptamines [ 31, several acetylcholine derivatives [4], narcotic analgesics [ 31, anticonvulsants [5], and pyridoxal amino acid Schiffs bases [6,7], in addition to numerous pesticides and several proprietary compounds. CAMSEQ has also been used to successfully predict octanol-water partition coefficients [8] and the conformational properties of several glycosaminoglycans [9, lo].…”

Section: Introductionmentioning

confidence: 99%

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Conformational energy calculations of some amphetamine analogs using a new solvation model

Weintraub

Nichols

2009

Int. J. Quantum Chem.

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A new model is proposed for the calculation of the solvation effect for hydrogen-bonded ionic species. The model is applied to a group of phenethylamine and amphetamine derivatives possessing a cationic ammonium group. This N+H, moiety is common among many compounds of biological interest. A detailed description of the solvation model is presented. The conformational properties of the amphetamine derivatives 2,5-dimethoxy-4-methyl-amphetamine (DOM), "ethyl DOM," and "cyclopropyl DOM" are discussed and an "active conformer" is proposed. The CAMSEQ software system was employed in this study.

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Section: Solvent Modelmentioning

confidence: 99%

“…The details of this calculation are discussed elsewhere [2,3,. The problem of determining the volume of intersection of a sphere with a cylindrical section is not trivial.(!)…”

Section: Solvent Modelmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Conformational energy calculations of some amphetamine analogs using a new solvation model

Weintraub

Nichols

2009

Int. J. Quantum Chem.

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“…The potential-energy curve is given in Figure 2 . Here, the results of former quantum-chemical calculations on chlorocholine taken as a reference for the gas phase will be compared with hydration shell studies within the CAMSEQ (conformational analysis of molecules in solution by empirical and quantummechanical techniques) version for the solvent water [8]. The CAMSEQ procedure includes the calculation of conformational energies by means of empirical potential functions (Lennard-Jones potential, Coulombic energy, hydrogenbonding energy.…”

Section: Pcilomentioning

confidence: 99%

Theoretical conformational analysis considering solvent effects

Hofmann

Peinel

Weller

1979

Int J of Quantum Chemistry

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“…The first predicts a preference for a gauche form [7], the second the near equivalence of the gauche and trans forms [8]. Finally, empirical (partitioned potential functions) Computations for isolated cationic phenethylamine and amphetamine predict a preference for a gauche form [9].…”

Section: Introductionmentioning

confidence: 99%

The exploration of the conformational properties of biological phenethylamines by molecular orbital techniques

Pullman

Berthod

Courrière

2009

Int. J. Quantum Chem.

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P c i L o computations using x-ray determined crystal geometry as input data indicate that the ytruche and ~I ' L I J I S conformers have practically identical energies in the majority of fundamental biological phenethylamines and phenethanolamines. Ah iriitio STO 3G computations indicate a small but definite preference of the isolated molecule for a guuche conformation. This result is confirmed for phenethylamine by an rib iriirio 4-31 G computation and by a computation using Clementi's 7s. 3pi3.s basis contracted to 2 v Ip!ls set. The exclusive occurrence of II"IJIS conformers in the CrySKaI and their preponderance in solution is attributed to the effect of environmental forces. Explicit computations on the effect of water. using the supermolecule approach, contirrn the tendency of the solvent to favor the rruns conformer.

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Conformational analysis of some phenethylamine molecules

Cited by 39 publications

References 22 publications

Conformational energy calculations of some amphetamine analogs using a new solvation model

Conformational energy calculations of some amphetamine analogs using a new solvation model

Theoretical conformational analysis considering solvent effects

The exploration of the conformational properties of biological phenethylamines by molecular orbital techniques

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