Abstract
The infrared and Raman characteristics of the cyclic dimer hydrogen-bonded carboxylic acid function in the solid state are fully reported. Some dicarboxylic acids (e.g., malonic, methylmalonic, di-methylmalonic, succinic, glutaric, and adipic acid) are reported as typical examples. The vibrational characteristics of the cyclic dimer hydrogen-bond pattern are studied through the effect of deuteration on the position of infrared and Raman bands and through the temperature effect on the behavior of the vibrational bands. The fundamentals can very well be compared with the fundamentals of the trans secondary amide function, and are therefore assigned as the acid I to acid VII fundamentals.
Keywords
Get full access to this article
View all access options for this article.
References
1.
Leiserowitz
L.
, Acta Cryst. B32 , 775 (1976 ).
2.
Benghiat
V.
Kaufman
H. W.
Leiserowitz
L.
and
Schmidt
G. M. J
, J. Chem. Soc., Perkin Trans. II , 1758 (1972 ).
3.
Slootmaekers
B.
and
Desseyn
H. O
, Appl. Spectrosc. 45 , 118 (1991 ).
4.
Wolfs
I.
Desseyn
H. O.
and
Perlepes
S. P
, Spectrochim. Acta 51A , 1147 (1994 ).
5.
Morrison
J. D.
and
Robertson
J. M
, J. Chem. Soc. 1001 (1949 ).
6.
Broadley
J. S.
Cruickshank
D. W. J.
Morrison
J. D.
Robertson
J. M.
Shearer
F. R.
and
Shearer
H. M. M
, Proc. R. Soc. London 251 , 441 (1959 ).
7.
Housty
J.
and
Hospital
M
, Acta Cryst. 18 , 693 (1965 ).
8.
Derissen
J. L.
, Acta Cryst. B26 , 901 (1970 ).
9.
Goedkoop
J. A.
and
MacGillavry
C. H
, Acta Cryst. 10 , 125 (1957 ).
10.
Bougeard
D.
De Villepin
J.
and
Novak
A
, Spectrochim. Acta 44A , 1281 (1988 ).
11.
Maury
L.
and
Bardet
L
, J. Raman Spectrosc. 7 , 197 (1978 ).
12.
Maury
L.
and
Bardet
L
, J. Raman Spectrosc. 8 , 345 (1979 ).
13.
Maréchal
Y.
, Chem. Phys. 79 , 69 (1983 ).
14.
Maréchal
Y.
, Chem. Phys. 79 , 85 (1983 ).
15.
Auvert
G.
and
Maréchal
Y
, Chem. Phys. 40 , 51 (1979 ).
16.
Gutmann
V.
, The Donor Acceptor Approach to Molecular Interactions (Plenum Press , New York , 1978 ).
17.
Bratos
S.
Ratajczak
H.
and
Viot
P
, in Hydrogen Bonded Liquids ,
Dore
J. C.
and
Teixeira
J
, Eds. (Kluwer Academic Publishers , The Netherlands , 1991 ), p. 221 .
18.
Maréchal
Y.
, in Hydrogen Bonded Liquids ,
Dore
J. C.
and
Teixeira
J
, Eds. (Kluwer Academic Publishers , The Netherlands , 1991 ), p. 237 .
19.
Maréchal
Y.
, Can. J. Chem. 63 , 1684 (1985 ).
20.
Claydon
M. F.
and
Sheppard
N
, J. Chem. Soc. Chem. Coram. , 1431 (1969 ).
21.
Bratoz
S.
Hadzi
D.
and
Sheppard
N
, Spectrochim. Acta 8 , 249 (1956 ).
22.
Millen
D. J.
, J. Mol. Struct. 100 , 351 (1983 ).
23.
Dybal
J.
Cheam
T. C.
Krimm
, J. Mol. Struct. 159 , 183 (1987 ).
24.
Desseyn
H. O.
, in The Chemistry of Acid Derivatives ,
Pataï
S.
, Ed. (John Wiley and Sons , Chichester , 1992 ), Vol. 2 , p. 271 .
25.
Nakamoto
K.
and
Kishada
S
, J. Chem. Phys. 41 , 1554 (1964 ).
26.
Nakamoto
K.
and
Kishada
S
, J. Chem. Phys. 41 , 1558 (1964 ).
27.
Fukushima
K.
and
Zwolinski
B. J
, J. Chem. Phys. 50 , 737 (1969 ).
28.
Wolfs
I.
and
Desseyn
H. O
, J. Mol. Struct. (Theochem) 360 , 81 (1996 ).