Behavior of the 9-anthryl-tert-butylcarbinol as a chiral solvating agent. Study of diastereochemical association by intermolecular NOE and molecular dynamics calculations

M. De Moragas; E. Cervelló; A. Port; C. Jaime; A. Virgili; B. Ancian

doi:10.1021/jo980261f

Behavior of the 9-anthryl-tert-butylcarbinol as a chiral solvating agent. Study of diastereochemical association by intermolecular NOE and molecular dynamics calculations

M. De Moragas, E. Cervelló, A. Port, C. Jaime, A. Virgili, B. Ancian

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

20 Citations (Scopus)

Abstract

The 9-anthryl-tert-butylcarbinol was tested as a chiral solvating agent (CSA) in the presence of racemic forms of mentil-p-toluenesulfinate, 9-(1- amino-2,2-dimethylpropyl)-9,19-dihydroanthracene, α-methoxyphenylacetic acid and 1-phenyl-1,2-ethanediol. Diastereomeric complexes were found to form between each enantiomer of these last two compounds. One of the enantiomers of 9-anthryltert-butylcarbinol was studied by means of intermolecular NOE and molecular dynamics calculations. Major thermodynamic and structural differences were found.

Original language	English
Pages (from-to)	8689-8695
Journal	Journal of Organic Chemistry
Volume	63
Issue number	24
DOIs	https://doi.org/10.1021/jo980261f
Publication status	Published - 27 Nov 1998

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title = "Behavior of the 9-anthryl-tert-butylcarbinol as a chiral solvating agent. Study of diastereochemical association by intermolecular NOE and molecular dynamics calculations",

abstract = "The 9-anthryl-tert-butylcarbinol was tested as a chiral solvating agent (CSA) in the presence of racemic forms of mentil-p-toluenesulfinate, 9-(1- amino-2,2-dimethylpropyl)-9,19-dihydroanthracene, α-methoxyphenylacetic acid and 1-phenyl-1,2-ethanediol. Diastereomeric complexes were found to form between each enantiomer of these last two compounds. One of the enantiomers of 9-anthryltert-butylcarbinol was studied by means of intermolecular NOE and molecular dynamics calculations. Major thermodynamic and structural differences were found.",

author = "{De Moragas}, M. and E. Cervell{\'o} and A. Port and C. Jaime and A. Virgili and B. Ancian",

year = "1998",

month = nov,

day = "27",

doi = "10.1021/jo980261f",

language = "English",

volume = "63",

pages = "8689--8695",

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Behavior of the 9-anthryl-tert-butylcarbinol as a chiral solvating agent. Study of diastereochemical association by intermolecular NOE and molecular dynamics calculations. / De Moragas, M.; Cervelló, E.; Port, A.; Jaime, C.; Virgili, A.; Ancian, B.

In: Journal of Organic Chemistry, Vol. 63, No. 24, 27.11.1998, p. 8689-8695.

Research output: Contribution to journal › Article › Research › peer-review

TY - JOUR

T1 - Behavior of the 9-anthryl-tert-butylcarbinol as a chiral solvating agent. Study of diastereochemical association by intermolecular NOE and molecular dynamics calculations

AU - De Moragas, M.

AU - Cervelló, E.

AU - Port, A.

AU - Jaime, C.

AU - Virgili, A.

AU - Ancian, B.

PY - 1998/11/27

Y1 - 1998/11/27

N2 - The 9-anthryl-tert-butylcarbinol was tested as a chiral solvating agent (CSA) in the presence of racemic forms of mentil-p-toluenesulfinate, 9-(1- amino-2,2-dimethylpropyl)-9,19-dihydroanthracene, α-methoxyphenylacetic acid and 1-phenyl-1,2-ethanediol. Diastereomeric complexes were found to form between each enantiomer of these last two compounds. One of the enantiomers of 9-anthryltert-butylcarbinol was studied by means of intermolecular NOE and molecular dynamics calculations. Major thermodynamic and structural differences were found.

AB - The 9-anthryl-tert-butylcarbinol was tested as a chiral solvating agent (CSA) in the presence of racemic forms of mentil-p-toluenesulfinate, 9-(1- amino-2,2-dimethylpropyl)-9,19-dihydroanthracene, α-methoxyphenylacetic acid and 1-phenyl-1,2-ethanediol. Diastereomeric complexes were found to form between each enantiomer of these last two compounds. One of the enantiomers of 9-anthryltert-butylcarbinol was studied by means of intermolecular NOE and molecular dynamics calculations. Major thermodynamic and structural differences were found.

U2 - 10.1021/jo980261f

DO - 10.1021/jo980261f

M3 - Article

VL - 63

SP - 8689

EP - 8695

IS - 24

ER -