Read e-book online Advanced Organic Chemistry. Reactions and Synthesis PDF

By Carey F., Sundberg R.

ISBN-10: 0306462443

ISBN-13: 9780306462443

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Therefore, to some degree, octupolar tetrachloromethane is also a kind of polar solvent. However, the intermolecular interaction energy rapidly falls o¤ at higher orders of the multipole [26d]. 2 Intermolecular Forces 13 chair-configured, non-dipolar solvent 1,4-dioxane, which often behaves like a polar solvent even though its relative permittivity is low (er ¼ 2:2), is caused by its large nonideal quadrupolar charge distribution [411]. 3 Dipole-Induced Dipole Forces [32] The electric dipole of a molecule possessing a permanent dipole moment m can induce a dipole moment in a neighbouring molecule.

Based on the type of orbitals involved in bonding interactions, all EPD molecules can be divided into three groups [51, 53]: n-, s-, and p-EPD. In the first group, the energetically highest orbital is that of the lone pair of n-electrons on the heteroatoms (R2 O, R3 N, R2 SO), in the second it is that of the electron pair of a s-bond (RaaHal, cyclopropane), and in the third it is that of the pair of p electrons of unsaturated and aromatic compounds (alkenes, alkylbenzenes, polycyclic aromatics).

The bond dissociation enthalpy for normal hydrogen bonds is ca. 13 . . 42 kJ/mol (3 . . 10 kcal/mol)*). For comparison, covalent single bonds have dissociation enthalpies of 210 . . 420 kJ/mol (50 . . 100 kcal/mol). Thus, hydrogen bonds are approx. ten times weaker than covalent single bonds, but also approx. ten times stronger than the non- Fig. 2-4a. Three types of circular hydrogen bonds: (a) homodromic, (b) antidromic, and (c) heterodromic hydrogen bonds [193]. * Bond dissociation enthalpies outside these limits are, however, known.

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Advanced Organic Chemistry. Reactions and Synthesis by Carey F., Sundberg R.

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