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.
Imai
Yoshitane
Y
Kuroda Chiromorphology Project, Japan Science and Technology Corporation, ERATO, Tokyo, Japan.
Tajima
Nobuo
N
Sato
Tomohiro
T
Kuroda
Reiko
R
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