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Synthesis

Debating ‘Most Polar’

July 27, 2015 | APPEARED IN VOLUME 93, ISSUE 30

A News of the Week article claimed that all-cis hexafluorocyclohexane (HFC) with a dipole moment equal to 6.2 debyes is “the most polar nonionic compound now known to exist” (C&EN, March 30, page 5). Without prejudice to the beautiful structure of this compound and its impressive synthesis, I would like to question this statement.

My coauthors and I described 4,5-bis(dimethylamino)-1,8-naphthalenedicarboxaldehyde, whose dipole moment is equal to 9.2 debyes owing to the effective conjugation of two pairs of dimethylamino and aldehyde groups (Zh. Org. Khim. 1991,27, 1536).

I feel certain that other similar examples exist. The above C&EN statement would be more correct with the following amplification: “All-cis HFC is probably the most polar among now known fully saturated nonionic compounds.”

Alexander F. Pozharskii
Rostov-on-Don, Russia

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