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Volumn 10, Issue 4, 2010, Pages 1749-1756

Spontaneous resolution of enantiomers by crystallization: Insights from computed crystal energy landscapes

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EID: 77950829438     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg9014306     Document Type: Article
Times cited : (38)

References (64)
  • 1
    • 77950818230 scopus 로고    scopus 로고
    • Guidance Document; U.S. Food and Drug Administration: Silver Spring, MD, January 5, 1992.
    • Development of New Stereoisomeric Drugs; Guidance Document; U.S. Food and Drug Administration: Silver Spring, MD, January 5, 1992; http://www.fda.gov/ Drugs/GuidanceComplianceRegulatoryInformation/Guidances/ucm122883.htm.
    • Development of New Stereoisomeric Drugs
  • 24
    • 77950815281 scopus 로고    scopus 로고
    • Note that this argument relies on the entropy of macroscopic mixing of homochiral crystals of opposite enantiomers in the conglomerate mixture being negligible and the racemic crystal having zero entropy at 0 K (as all ordered crystals); that is, there is no configurational (residual) entropy contribution because of the presence of two enantiomers in the unit cell. The term RT ln 2 appears, and rightly so, in all thermodynamic cycles (4, 7, 23) to compute the free energy of racemic formation (1) from the heat of fusion of the pure enantiomer, the heat of fusion of the racemic mixture, and the corresponding melting points. This is because the pure enantiomer is in equilibrium with the enantiopure (and not the racemic) liquid.
    • Note that this argument relies on the entropy of macroscopic mixing of homochiral crystals of opposite enantiomers in the conglomerate mixture being negligible and the racemic crystal having zero entropy at 0 K (as all ordered crystals); that is, there is no configurational (residual) entropy contribution because of the presence of two enantiomers in the unit cell. The term RT ln 2 appears, and rightly so, in all thermodynamic cycles (4, 7, 23) to compute the free energy of racemic formation (1) from the heat of fusion of the pure enantiomer, the heat of fusion of the racemic mixture, and the corresponding melting points. This is because the pure enantiomer is in equilibrium with the enantiopure (and not the racemic) liquid.
  • 45
    • 77950805566 scopus 로고    scopus 로고
    • version 1.05, is a substantial revision of DMAREL
    • Welch, G. W. A.; Karamertzanis, P. G.; Price, S. L.; Leslie, M. DMACRYS, version 1.05, is a substantial revision of DMAREL; 2010; http://www.chem.ucl.ac. uk/cposs/dmacrys/
    • (2010) DMACRYS
    • Welch, G.W.A.1    Karamertzanis, P.G.2    Price, S.L.3    Leslie, M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.