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39. A. F. Reid, H. K. Perkins, and M. J. Sienko, Inorg. Chem. 7, 119 (1968). 40. K. A. Wickersheim and 1~. A. Lefever, J. Chem. Phys. 36, 844 (1962). 41. R. V. Pisarev, Soy. Phys. Solid State, 6, 2026 (1965). 42. P. C. Bailey, J. Appl. Phys. 31, 39 (1960). 43. W. L. Baun and N. T. McDevitt, J. Amer. Ceram. Soc. 46, 294 (1963). 44. J. A. Goldsmith and S. D. Ross, Spectroehim. Acta 23A, 1909 (1967). 45. R. Marshall, S. S. Mitra, P. J. Gielisse, J. N. Plendl, and L. C. Mansur, J. Chem. Phys. 43, 2893 (1965). 46. D. R. Renneke and D. N. Lynch, Phys. Rev. 138, A530 (1965). 47. D. A. Brown, D. Cunningham, and W. K. Glass, Spectrochim. Acta 24A, 965 (1968). 48. C. N. R. Rao, Chemical Applications of Infrared Spectroscopy (Academic, New York, 1963). 49. F. Petru and M. Muck, Z. Chem. 7, 159 (1967). 50. V. G. Gatt6w and 0. Glemser, Z. Anorg. Allgem. Chem. 309, 121 (1961).
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Vibrational Spectra of Isomeric Aminophenols V. N. Verma and D. K. Rai Department of Spectroscopy, Banaras Hindu University, Varanasi-5, India
(Received 21 October 1969; revision received 13 February 1970) The ir absorption spectra of the isomeric aminophenols have been recorded~in-the ranger250-4000 cm-1. The observed bands have been analyzed in terms of fundamentals, combinations, and overtones of a number of frequencies. These frequencies have been assigned to different'modes of vibrations. INDEX HEADINGS: Infrared spectra; Vibrational assignments; Isomeric aminophenols.
INTRODUCTION "-~A l a r g e a m o u n t of w o r k on t h e s p e c t r a of s u b s t i t u t e d a n i l i n e s a n d p h e n o l s h a s b e e n r e p o r t e d in t h e literature. Jakobsen and Brewer 1 have studied the v i b r a t i o n a l s p e c t r a of p - s u b s t i t u t e d p h e n o l s in t h e r a n g e 3 0 0 - 1 7 0 0 e m -1. T h e R a m a n s p e c t r a of o- a n d m-aminophenols have been reported by Hertz and K o h l r a u s c h 2 a n d of p - a m i n o p h e n o l b y P a u l s e n 2 T h e e l e c t r o n i c a b s o r p t i o n s p e c t r u m of o - a m i n o p h e n o l h a s been studied by Sharma and Rao. 4 The present work h a s b e e n u n d e r t a k e n t o p r o v i d e as c o m p l e t e a s t u d y of t h e v i b r a t i o n a l s p e c t r a of t h e t h r e e i s o m e r i c a m i n o p h e n o l s as is p r e s e n t l y possible. T o s u p p l e m e n t t h e R a m a n a n d i r d a t a a l r e a d y a v a i l a b l e in t h e a b o v e m e n t i o n e d references, n e w ir s p e c t r a h a v e b e e n recorded.
I. EXPERIMENTAL T h e s a m p l e s of t h e i s o m e r i c a m i n o p h e n o l s u s e d in t h e s e s t u d i e s w e r e f r o m B . D . H . , U . K . a n d w e r e of c h e m i c a l l y p u r e q u a l i t y . T h e s e were f u r t h e r p u r i f i e d b y r e p e a t e d r e c r y s t a l l i z a t i o n f r o m a s o l u t i o n in a
m i x t u r e of a l c o h o l a n d w a t e r in t h e r a t i o 1:2. T h e t h r e e i s o m e r i c a m i n o p h e n o l s w e r e u s e d i n t h e f o r m of a n u j o l m u l l for r e c o r d i n g of t h e i r t r a c e s . T h e s p e c t r a w e r e r e c o r d e d in t h e r a n g e 2 5 0 - 4 0 0 0 e m -1 o n a P e r k i n E l m e r m o d e l 521 g r a t i n g s p e c t r o p h o t o m e t e r . T h e ir s p e c t r u m of p - a m i n o p h e n o l h a s also b e e n r e c o r d e d in t h e f o r m of a p e l l e t a f t e r m i x i n g i t w i t h K B r p o w d e r . T h e g r a t i n g i n s t r u m e n t u s e d in t h e p r e s e n t i n v e s t i g a t i o n s h a s a r e s o l u t i o n 0.3 e m -1 a t 1000 e m -1 a n d t h e m e a s u r e d f r e q u e n c i e s a r e e x p e c t e d t o b e a c c u r a t e to ~ 0 . 5 e m -1. T h e s p e c t r a a r e r e p r o d u c e d in Figs. 1-3.
II. RESULTS A N D DISCUSSIONS T h e i d e n t i f i c a t i o n of t h e s y m m e t r y g r o u p a p p r o p r i a t e to s u b s t i t u t e d b e n z e n e m o l e c u l e s is m o r e c o m p l i c a t e d w h e n t h e s u b s t i t u e n t is n o t a single a t o m b u t a g r o u p of a t o m s . R a n d l e a n d W h i f f e n 5 in t h e i r d i s c u s s i o n s of v i b r a t i o n a l s p e c t r a of m o n o s u b s t i t u t e d b e n z e n e s h a v e s h o w n t h a t a g r o u p of a t o m s m a y b e a p p r o x i m a t e l y t r e a t e d l i k e a single a t o m since t h e l o c a l s y m m e t r y of t h e b e n z e n e r i n g is n o t m u c h aff e c t e d b y t h e s u b s t i t u e n t . I f we a s s u m e t h a t t h e NI-I2
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