TY - JOUR
T1 - Normal boiling points of 1,ω-alkanedinitriles
T2 - The highest increment in a homologous series
AU - Balaban, Alexandru T.
AU - Basak, Subhash C
AU - Mills, Denise
PY - 1999
Y1 - 1999
N2 - The normal boiling point for cyanogen is -22 °C; for its next homologue, malononitrile, it is 219 °C. The difference of 241 °C is apparently the highest one encountered for the addition of a single methylene group. Problems connected with boiling points and a rationalization for this observation are discussed in the context of intermolecular forces for liquids. A quantitative structure-property relationship (QSPR) study of the normal boiling points for monohaloalkanes and for the corresponding nitriles is reported. The behavior of the nitrile group as a pseudohalogen is also discussed. Normal boiling points of compounds having a cyano group bonded to an electron-attracting substituent situate the CN group close to being a pseudohalogen, but when the CN group is bonded to electron-donor substituents, the situation changes.
AB - The normal boiling point for cyanogen is -22 °C; for its next homologue, malononitrile, it is 219 °C. The difference of 241 °C is apparently the highest one encountered for the addition of a single methylene group. Problems connected with boiling points and a rationalization for this observation are discussed in the context of intermolecular forces for liquids. A quantitative structure-property relationship (QSPR) study of the normal boiling points for monohaloalkanes and for the corresponding nitriles is reported. The behavior of the nitrile group as a pseudohalogen is also discussed. Normal boiling points of compounds having a cyano group bonded to an electron-attracting substituent situate the CN group close to being a pseudohalogen, but when the CN group is bonded to electron-donor substituents, the situation changes.
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U2 - 10.1021/ci9900074
DO - 10.1021/ci9900074
M3 - Article
AN - SCOPUS:0006027738
SN - 0095-2338
VL - 39
SP - 769
EP - 774
JO - Journal of chemical information and computer sciences
JF - Journal of chemical information and computer sciences
IS - 5
ER -