Molecular recognition in solid-state crystallization: colored chiral adduct formations of 1,1'-bi-2-naphthol derivatives and benzoquinone with a third component.
Molecular recognition in solid-state crystallization involving derivatives of 1,1'-bi-2-naphthol and benzoquinone was studied. No adduct crystal was formed when crystals of biphenyl were further added as a third component to a grinding mixture of crystals of chiral 1,1'-bi-2-naphthol and benzoquinone, which by itself did not form an adduct. This contrasts with the case in which further addition of naphthalene crystals to the same mixture produced a new red crystal. Adduct formations using chiral 6,6'-dibromo-1,1'-bi-2-naphthol in place of 1,1'-bi-2-naphthol were also studied. In this case, adducts were produced either with or without biphenyl as a third compound, but the colors of the adducts differed significantly in the two cases: red and bluish-black. The same three-component adduct crystals were produced from solid-grinding and solution crystallization and the structure was determined by X-ray diffractometry. Based on the crystal structures, theoretical calculations were carried out to compare the mechanism of colorations in the binary and the ternary complexes.
Kuroda Chiromorphology Project, Japan Science and Technology Corporation, ERATO, Tokyo, Japan.
Yoshitane
Y
Imai
Nobuo
N
Tajima
Tomohiro
T
Sato
Reiko
R
Kuroda
D016227:Benzoquinones / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008956:Models, Chemical; D008958:Models, Molecular; D009284:Naphthols / Q000737:chemistry*; D013237:Stereoisomerism
D016227:Benzoquinones; D009284:Naphthols; C004532:quinone; C412332:1,1'-bi-2-naphthol