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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 28, Number 1
BKCSDE 28(1)
January 20, 2007 

The 3-[3α(2α-Hydroxy)pinane]-4,5-(pinan)-1,3-oxazolidine Synthesis, Structure and Properties
Magdalena Bialek*, Agata Trzesowska, Rafal Kruszynski
Pinane, Natural bonding orbital, Oxazolidine, Crystal and molecular structure, Electronic structure
The new pinane derivative containing unique multifused ring system was synthesized. The crystal, molecular and electronic structure of the title compound has been determined. Both pinane ring systems have the same conformation. The five-membered oxazolidine ring exists in twisted chair conformation. The structure is expanded through O-H…O hydrogen bond to semiinfinite hydrogen-bonded chain. The bond lengths and angles in the optimised structure are similar to the experimental ones. The CH3 and CH2 groups (except this of oxazolidine ring) are negatively charged whereas the CH groups are positively charged. The largest negative potential is on the oxygen atoms. The C-N natural bond orbitals are polarised towards the nitrogen atom (ca. 61% at N) whereas the C-O bond orbitals are polarised towards the oxygen atom (ca. 67% at O). It is consistent with the charges on the nitrogen and oxygen atom of oxazolidine ring and the direction of the dipole moment vector (3.08 Debye).
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