Conformations of Benzyl Alcohols

Conformational Preferences and Pathways for Enantiomerization and Diastereomerization of Benzyl Alcohol. Data Mining and ab Initio Quantum-Mechanical Study.

Rainer Glaser* and G. Richard Nichols

Department of Chemistry
University of Missouri-Columbia
Columbia, Missouri, 65211 (USA)

A CHIME plugin is required for the display of the pdb files of the following structures.

Figure 1. Molecules 1a (1a), 1b (1b) & 1c (1c) at MP2(full)/6-31G* (RHF/6-31G*)

Figure 2. Molecules 2a (2a) & 2b (2b) at MP2(full)/6-31G* (RHF/6-31G*)

Figure 3. Molecules 3a (3a), 3b (3b) & 3d (3d) at MP2(full)/6-31G* (RHF/6-31G*)

Table 1. Conformational Properties of Crystal Structures of Benzyl Alcohols.

CSD Record	(O-C-C-C)	C-C type	(H-O-C-C)	O-C type
Benzyl Alcohol
DEBGOG	18.6	Staggered	112.5	Cis, C-H
FAXLAR	8.3	Eclipsed
JATNIB	10.0	Eclipsed
WIHCEV	24.0	Staggered
WILJAC	67.6	Stag. Perp.
YOVVAG	72.0	Stag. Perp.	175.0	Trans

BnOH Derivatives
BAGBAM	-76.0	Stag. Perp.	-163.4	Trans
	-5.2	Eclipsed	-144.0	Cis, C-H
BHHPHE	16.3	Staggered	-171.6	Trans
BZALPZ	-12.5	Eclipsed	77.8	Gauche
	-80.2	Stag. Perp.	60.7	Gauche
CAGZIT	16.8	Staggered	-161.9	Trans
CEBTIZ	65.4	Stag. Perp.	66.4	Gauche
CIZWOX	37.0	Staggered	41.4	Gauche
CUJVOS	-78.2	Stag. Perp.	-32.0	Gauche
	-9.0	Eclipsed	159.8	Trans
	-65.6	Stag. Perp.	-58.4	Gauche
CUJVUY	40.2	Staggered	-140.3	Cis, C-H
	74.6	Stag. Perp.	-92.9	Cis, C-H
	-87.4	Stag. Perp.	-28.6	Cis, C-C
	-2.8	Eclipsed	34.9	Gauche
DESKOB	-63.2	Stag. Perp.	-55.5	Gauche
	-2.9	Eclipsed	79.4	Gauche
DEZLOJ	-10.0	Eclipsed	-126.0	Cis, C-H
DINWIG	68.0	Stag. Perp.
EABTIZ	73.5	Stag. Perp.	179.5	Trans
EMERIC	71.8	Stag. Perp.	-76.3	Gauche
FAMHEG	2.4	Eclipsed	85.2	Gauche
	-69.4	Stag. Perp.	-31.2	Gauche
FUPLAD	75.9	Stag. Perp.	76.9	Gauche
	30.5	Staggered	66.3	Gauche
GAKNAH	52.7	Staggered	173.4	Trans
GASJOZ	72.0	Stag. Perp.
HYCANM	72.0	Stag. Perp.	46.3	Gauche
JUGPAC	-13.8	Eclipsed	72.5	Gauche
	-82.4	Stag. Perp.	160.4	Trans
JUWZAC	45.6	Staggered
KAWTOR	22.0	Staggered	66.4	Gauche
KEDKOT	-26.4	Staggered
KOFJEU	-85.5	Stag. Perp.
KOHJIA	12.7	Eclipsed	113.0	Cis, C-H
LIGYUW	-86.0	Stag. Perp.
MDSPBF	23.0	Staggered
	-67.6	Stag. Perp.
MMXDPA	-19.3	Staggered
NADGEE	12.4	Eclipsed
	0.0	Eclipsed
OHIBNZ	-14.5	Eclipsed
PAMJES	7.4	Eclipsed
RAVREL	-7.9	Eclipsed	-70.0	Gauche
	-66.8	Stag. Perp.	159.0	Trans
SALBUT	-87.8	Stag. Perp.
	81.3	Stag. Perp.	43.0	Gauche
SAZCIF	-8.4	Eclipsed
	-8.4	Eclipsed	95.0	Cis, C-H
SAZHEG	58.8	Staggered	65.3	Gauche
SPPHOS	-9.8	Eclipsed
	-79.7	Stag. Perp.
TEKKEZ	68.6	Stag. Perp.	66.3	Gauche
	70.0	Stag. Perp.	-156.8	Trans
	-6.4	Eclipsed	72.8	Gauche
VEHREF	-20.9	Staggered
VICFOC	-2.8	Eclipsed
	1.0	Eclipsed
VUKCEJ	61.2	Stag. Perp.	-122.2	Cis, C-H
	-81.7	Stag. Perp.	-151.0	Trans
	-54.5	Staggered	139.3	Cis, C-H
	52.0	Staggered
WIDGIZ	86.0	Stag. Perp.
WISFOT	-86.9	Stag. Perp.	-67.0	Gauche
	-35.4	Staggered	-59.2	Gauche
	39.7	Staggered	-174.6	Trans
YALTEK	-4.2	Eclipsed	-117.7	Cis, C-H
	67.4	Stag. Perp.	-157.5	Trans
YELGUR	59.5	Staggered	29.4	Cis, C-C
YUNYOV	-80.8	Stag. Perp.
YUNYOV0	72.8	Stag. Perp.
YUNYUB	61.3	Stag. Perp.	22.6	Cis, C-C
	73.7	Stag. Perp.	40.5	Gauche
YUNZAI	-57.6	Staggered	-19.9	Cis, C-C
ZENVAP	59.4	Staggered
	46.5	Staggered
	46.0	Staggered
	46.3	Staggered
ZOXLAZ	4.6	Eclipsed	-67.6	Gauche

(a) All dihedral angles in degrees.

(b) C-C type determined by absolute value of the dihedral angle (O-C-C-C):
0-15 is "eclipsed," 15-60 is "staggered," and 60-90 is "staggered perpendicular."

(c) O-C type determined by absolute value of the dihedral angle (H-O-C-C):
0-30 is "cis, CC", 30-90 is "gauche", 90-150 is "cis, C-H", 150-180 is "trans".