“To Not” or “Not To”?

Sometimes one encounters in contract drafting issues that are of broader relevance. In MSCD, discussion of such issues is grouped in chapter 16, and on this blog they’re grouped in the category “Drafting as Writing.”

I encountered one such issue yesterday, when I received the following email from a reader:

I was wondering whether there is any difference in meaning between (A) “opt not to apply” and (B) “opt to not apply.” I was wondering if you could (or should) opt for (B), if you wanted to make the point that you deliberately decided to forego the application. You have any views on this? Many thanks.

I replied as follows:

Here’s what The New Fowler’s Modern English Usage 530 (3d ed.) has to say:

Not is routinely used before a to-infinitive, negating all that follows it: … She tried not to watch Oscar count out his farthings …. But, not uncommonly, not is placed between (‘splits’) the to and its infinitive: … It was wrong to not love them …. This ‘unprincipled’ placing of not is presumably intended to give additional emphasis to the negativity.

In the limited and stylized world of contract drafting, where you put the not doesn’t affect meaning. But to avoid antagonizing those who make a fetish of not splitting infinitives, I’d put the not before the to-infinitive.