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PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
1
pubmed:dateCreated
2009-1-8
pubmed:abstractText
Novel chiral binaphtyl surrogates with an inner hydrogen bond have been created. The NH appears at 13.0-13.3 ppm in thier (1)H NMR spectrum, indicating extremely strong hydrogen bonding. Enantiomers of these compounds were stable at ambient temperature and separable by HPLC with a chiral stationary phase. The half-lives of racemization of the enantiomer are in the range 3 months to 2 years at 20 degrees C, and the barriers for racemization are in the range 27.0 to 28.2 kcal/mol. An X-ray crystal analysis of the compound (R = CHPh(2)) shows that the pseudonaphthyl skeleton including CN...HN is almost completely planar and the dihedral angle between the pseudonaphthalene and naphthalene rings is 128 degrees .
pubmed:language
eng
pubmed:journal
pubmed:status
PubMed-not-MEDLINE
pubmed:month
Jan
pubmed:issn
1520-5126
pubmed:author
pubmed:issnType
Electronic
pubmed:day
14
pubmed:volume
131
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
54-5
pubmed:year
2009
pubmed:articleTitle
Axially chiral binaphthyl surrogates with an inner N-H-N hydrogen bond.
pubmed:affiliation
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan.
pubmed:publicationType
Journal Article