RICONThe Computer Program for the Quantitative Investigations of Cyclic Organic Molecule Conformations

Zotov, A. Yu.; Palyulin, V. A.; Зефиров, Н. С.

doi:10.1021/ci960115f

Cited by 39 publications

(15 citation statements)

References 37 publications

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“…The Cremer and Pople parameters were calculated with the RICON program. 26 Conversions from dihedral angles into vicinal coupling constants [ 3 J(H,H)] for each conformer were done using the Altona program. 21 Spectral simulations were achieved using version 2.3a of the MestRe-C program.…”

Section: Molecular Modeling Calculationsmentioning

confidence: 99%

DFT and NMR parameterized conformation of valeranone

Torres-Valencia

Meléndez-Rodrı́guez

Álvarez-García

et al. 2004

Magnetic Reson in Chemistry

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A Monte Carlo random search using molecular mechanics, followed by geometry optimization of each minimum energy structure employing density functional theory (DFT) calculations at the B3LYP/6-31G* level and a Boltzmann analysis of the total energies, generated accurate molecular models which describe the conformational behavior of the antispasmodic bicyclic sesquiterpene valeranone (1). The theoretical H-C-C-H dihedral angles gave the corresponding 1H, 1H vicinal coupling constants using a generalized Karplus-type equation. In turn, the 3J(H,H) values were used as initial input data for the spectral simulation of 1, which after iteration provided an excellent correlation with the experimental 1H NMR spectrum. The calculated 3J(H,H) values closely predicted the experimental values, excepting the coupling constant between the axial hydrogen alpha to the carbonyl group and the equatorial hydrogen beta to the carbonyl group (J(2beta, 3beta)). The difference is explained in terms of the electron density distribution found in the highest occupied molecular orbital (HOMO) of 1. The simulated spectrum, together with 2D NMR experiments, allowed the total assignment of the 1H and 13C NMR spectra of 1.

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Section: Molecular Modeling Calculationsmentioning

confidence: 99%

DFT and NMR parameterized conformation of valeranone

Torres-Valencia

Meléndez-Rodrı́guez

Álvarez-García

et al. 2004

Magnetic Reson in Chemistry

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“…According to the X-ray diffraction data and the results of puckering parameter calculations by the ZefirovPalyulin (ZP) [6] and Cremer-Pople (CP) [7] methods using the RICON program, [8] the six-membered phosphinoline ring in structure 18c was found to have a distorted skewboat conformation (ZP parameters: S = 0.201, θ = 61.6°, Finally, the reaction of 3-furyl-substituted ylide 16c with (4-methoxyphenyl)acetylene under UV irradiation (366 nm) gave phosphininofuran 18c, which was found to be identical to the sample obtained from 2-furyl-substituted ylide 14c. Moreover, the 1 H, 13 C, and 31 P NMR spectra of phosphininofuran 18c prepared from 2-(14c) and 3-furyl-substituted (16c) ylides were identical both for the separated samples and for their equimolar mixture.…”

Section: Resultsmentioning

confidence: 99%

Furyl‐Substituted Mixed Phosphonium–Iodonium Ylides in the Synthesis of Annelated P‐Containing Heterocyclic Compounds

et al. 2015

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Photochemical reactions between stabilized furyl‐substituted phosphonium–iodonium ylides and terminal acetylenes led to the formation of new P‐containing heterocyclic compounds. For the heterocyclization of 2‐furyl‐substituted ylides, we observed an unprecedented electrophilic ipso attack onto the α position of the furan ring in a carbocationic intermediate, leading – via a spiro intermediate – to the rearranged product with a 2,3‐shift in the furan ring.

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“…1). To estimate quantitatively the distortion of rings from standard conformations we have calculated Zefirov-Palyulin [6,7] as well as Cremer-Pople [8] puckering parameters for these rings in the structures 1 and 2. All these data were calculated by RICON [9] program and collected in the Table 1.…”

Section: Resultsmentioning

confidence: 99%

Molecular and crystal structure of indole derivatives fused with substituted bicyclo[3.3.1]nonane

et al. 2007

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Molecular structures of oxime 6-oxo-indolo[2,3-b]-bicyclo[3.3.1]non-2-en 1 and 6-oxo-(5-methoxyindolo[2,3-b])-bicyclo[3.3.1]non-2-en 2 were determined by X-ray crystal investigation. It was revealed that oxime 1 has anti-configuration in respect to indole-containing framework, and both compounds adopt half-chair-chairconformation. The distortion of rings was evaluated by calculation of the ZP-and CP-puckering parameters. The presence of the methoxy-group in compound 2 was found to lead to the changes in molecular packing in comparison with structure 1.

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RICONThe Computer Program for the Quantitative Investigations of Cyclic Organic Molecule Conformations

Cited by 39 publications

References 37 publications

DFT and NMR parameterized conformation of valeranone

DFT and NMR parameterized conformation of valeranone

Furyl‐Substituted Mixed Phosphonium–Iodonium Ylides in the Synthesis of Annelated P‐Containing Heterocyclic Compounds

Molecular and crystal structure of indole derivatives fused with substituted bicyclo[3.3.1]nonane

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