Proton Spin-Spin Coupling in Aromatic Molecules. p-Disubstituted

resonance of heterocyclic compounds related to anthracene. Norman E. Sharpless , Robert B. Bradley , James A. Ferretti. Organic Magnetic Resonance...
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P. F. Cox

380 1.5

7

Vol. 85 TABLE XI1 BEHAVIOR OF PHENOL IN “INERT” SOLVENT MIXTURES

Solvent mixtures CClr (20: 17 v . / v . ) Cyclohexane CClr 4- CSz (3:2 v./v.)

+

Cyclohexane

3639 3642

+ hexane (8: 1 + CCla (7: 1

Perfluorooctane w./w.) Perfluorooctane w./w.) FC-75&satd. with F C - 7 P satd. with

0 4U

03-

CCla cyclohexane

3639, 3624 (see tent and Fig. 12a) 3642, 3623 (see Fig. 12b) 3640, 3623 (similar to above) 3640 (slight asymmetry on low freq. side)

Or FC-75 is a mixture of perfluorocyclic ethers (Minnesota Mining and Mfg. Co.). Its behavior is very much like that of perfluorooctane, and it is much more readily available. The free band of phenol in FC-75 is at 3645 em.-’; there is no tendency to hydrogen bond to the oxygen atom in this solvent. Perfluorotributylamine (FC-47) behaves similarly in these respects, but solubilities are lower in this solvent.

02-

01

(1 : 1 v./v.)

Hexane f CSz (10:7 v./vJ

05-

o

+ C&

Y O H phenol, cm.-’ (max.) 3614 (symmetrical) 3606 (slight asymmetry on low freq. side) 3608 (definite asymmetry on low freq. side) 3614 (definite asymmetry on low freq. side)

-

0 cmrl, Fig. 12.-The appearance of the OH band of dilute phenol in hexane (8: 1 w./w.); (b) perfluorooctane (a) perfluorooctane 4- CCI, (7: 1 w./w.); concn. of phenol