Chlorine hydrogen bonds

If tetramethylammonium chloride is dissolved in hydrochloric acid, the unstable salt [(CH3)4N] [HClj], can be crystallised out here chlorine is showing weak hydrogen bonding (cf. F H—F which is stable, and Cl - H—Cl which is unstable). 

The relations 4- > 2-position in rate and 4- < 2-position in will apparently apply to reactions with anions, but the reverse relation is observed in piperidination, presumably due to 2-substitution being favored by hydrogen bonding in the zwitterionic transition state (cf. 47, 59, and 277) or by solvent-assisted proton removal from the intermediate complex (235). Substitutions of polychloroquino-lines (in which there is a combined effect of azine-nitrogen and unequal mutual activation of the chlorine substituents) also show 4- > 2-position in reactivity contrary statements are documented by these same references. Examples are cited below of the relation 2- > 4-position when a protonated substrate or a cyclic transition state is involved. 

Because of the electric interaction, hydrogen-bonded molecules hold on to each other more tightly than those in substances with pure covalent bonds. This cohesiveness is why water is a liquid at room temperature, whereas heavier covalent-bonded molecules such as chlorine, in the form of CI2, are gases. 

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