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- W2054292079 abstract "Two isomorphous crystal structures of inclusion compounds of the racemic cyclic monohydrazide of diphenic acid (6,7-dihydro-dibenzo[d,f][1,2]diazocine-5,8-dione) 1 with EtOH and MeCN are reported. In the crystals with space group C2/c the axially chiral enantiomers strictly alternate, forming zigzag tapes with an R22(8) H-bonding graph. (+)-1 was obtained by partial crystallization of the diastereomeric prolinomethyl derivatives 2 followed by acid cleavage of the auxiliary. The (R)-configuration of (+)-1 was established from the crystal structure of (R,S,S)-(+)366-2. The free activation energy for enantiomerization of 1 at 373 K was determined as ΔG‡=(126.7±0.8) kJ mol−1. The enantiomerization pathway was investigated using quantum-mechanical methods. At the DFT B3LYP/6-31G(d,p) level two enantiomeric C2-symmetric transition states and two enantiomeric pathways were found, with a calculated barrier of 155.6 kJ mol−1. The pathways can be divided into two steps, one involving primarily inversion of the amidic bridge, the other movement of the aromatic rings. CD-spectra of (R)-1 agree with previously published data on twisted biphenyls." @default.
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- W2054292079 date "2004-02-01" @default.
- W2054292079 modified "2023-10-14" @default.
- W2054292079 title "Cyclic diphenic hydrazide: crystal structure, resolution, absolute configuration, and enantiomerization pathway investigation" @default.
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- W2054292079 doi "https://doi.org/10.1016/j.tetasy.2003.12.003" @default.
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