To Not or Not To

To Not vs Not To

By Stephen M Golden

People use “to not” and “not to” interchangeably in language. Is there a difference between their position in a sentence? Some will argue that “to not” results in a split infinitive.

That means the “to” is separated from its verb, such as the verb “to eat” is split as “to not eat”. The proper construction would be “not to eat.” However, with so much other abuse of the English language having become acceptable, such as plural pronouns being accepted with singular entities and so on, the “split infinitive” distinction is beyond the comprehension of most people. Some grammarians are even concluding split infinitives are acceptable if it makes the sentence clearer.

I would say that such consideration is important in every case. I submit that “to not” and “not to” mean different things. The difference is subtle, like the difference between “supposedly” and “supposably” (also here), but there is a difference in meaning.

For example,

“I advise you not to take the highway,” carries the meaning that the person does not advise you to take the highway. In other words, he’s not encouraging you to take the highway. You could rephrase it as, "I'm not advising you to take the highway" or “I don’t advise you to take the highway.”

“I advise you to not take the highway,” carries the meaning that the person advises you to not take the highway. In which case, he is directly advising you that you should not take the highway. You could rephrase it as “You should not take the highway.”

Is “not to” more decisive or emphatic?

Well, aside from being historically, grammatically correct, "not to" is less emphatic. It's almost like saying "I'm not advising you to take the highway."

While "to not," even though it is historically, grammatically incorrect, is saying, "Don't take the highway."

In other contexts, the emphatic difference varies.

For example,

"I'm asking you to keep your voice low to not wake your father."

vs.

"I'm not asking you to keep your voice low not to wake your father, but to not wake the baby."

“Not to” says, “I’m not asking you to do it” whereas “to not” says, "I’m asking you to not do it.”

Another example:

“I invested in this stock. This is not to give you financial advice.”

“I won’t tell you what stock I chose. This is to not give you financial advice.”

Another example:

Our goal is not to keep her from dying. (We have a different goal than to keep her from dying.)

Our goal is to not keep her from dying. (We do not wish to prevent her from dying.)