The melting point alternation in α,ω-alkanedicarboxylic acids

Journal of the American Chemical Society

Volumn 122, Issue 38, 2000, Pages 9227-9236

  Thalladi, Venkat R ^a   Nüsse, Markus ^a   Boese, Roland ^a  

^a UNIVERSITY OF DUISBURG ESSEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE DERIVATIVE; CARBENE; CARBON; CARBOXYLIC ACID DERIVATIVE; CARBROMAL;

ARTICLE; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; DENSITY; ENERGY; HYDROGEN BOND; HYDROPHOBICITY; MELTING POINT; MOLECULAR MODEL; PHASE TRANSITION; SOLID; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0041112482     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0011459     Document Type: Article

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67. These data are also useful for those who are dealing with solid-state properties at variable temperatures. For example, van der Waals radii of many atoms have been found to vary with temperature: Kirchner, M. T.; Boese, R., unpublished results.
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72. This is also conformed by the accurate H-atom positions obtained from the neutron diffraction data from the C8-diacid made at three different temperatures (ref 121).
73. The closest C⋯O distances at 130 K in Å units are as follows: C4 (3.277), C5 (3.274), C6 (3.159), β-C7 (3.194), C8 (3.116), β-C9 (3.169), and C10 (3.086).
74. The density trend is similar for the data at 298 K too; see Supporting Information.
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77. Concomitant polymorphism is also reported for C9-diacid (ref 11c). For a review on this phenomenon, see: Bernstein, J.; Davey, R. J.; Henck, J.-O. Angew. Chem., Int. Ed. 1999, 38, 3440.
78. Twisting of carboxy groups also seem to result in somewhat longer hydrogen bonding separations in the odd members. The O⋯O distances for even and odd diacids are given in Table 4. It may be noted that the differences are at the second decimal place, and the difference in their contribution to the overall packing energy, although detectable, is very little.
79. The packing coefficients follow a trend similar to that of densities, that is, they are inversely correlated with the melting points. See Tables 2 and 3 and also Supporting Information for a graphical display.
80. Many other possibilities could be imagined with various degrees of inclination of adjacent dimers, but only those possibilities are realized which confer stability to the overall packing. Further polymorphs suggested in a recent study (ref 12m) could well belong to one of these possibilities.
81. Cotterill, R. M. J. (J. Cryst. Growth 1980, 48, 582) eloquently expresses the following in his article entitled "The Physics of Melting": "It is interesting to note that of all the physical phenomena known to man, some of the most common have proved to be the most difficult to understand. Melting is a case in point. The ultimate transition from the crystalline state to the liquid state, at a sufficiently high temperature, remains a mystery."
82. Our work is largely confined to providing an answer to the alternating melting point riddle well-known in n-alkanes and their derivatives. However, the even-odd carbon atom disparity is much more general (see: Sarma, J. A. R. P.; Nangia, A.; Desiraju. G. R.; Zass, E.; Dunitz, J. D. Nature 1996, 384, 320).