[Prax Cortez]

What's the difference in usage between not to and to not? How do we explain it grammatically? Can anyone give examples of sentences showing the difference?

[susan53]

I'm not exactly sure what you mean here, but I imagine to + infinitive, eg I told you not to do it!.

In this context (ie with tell) it would be much more usual to place the negation before to+ infinitive -I searched for both in a Concordancer and came up with only one example of tell + to + not ...
a memo a few days ago to Republican candidates telling them to not hesitate to run against the
versus the full 40 (the maximum the programme will provide) for tell + to + not

However, in other contexts lots of examples came up, including the first one below which has three examples strung together :
... fun to not make stupid faces into the camera to not move around to not cross our arms and most ...
... she claims to not like the song ...
if a juror wanted to not believe Mr. King,...
You'd have to be cynical to the marrow to not feel it as so much more.

To me, all of these sound awkward - in each case I'd generally move the negation before to - but it is frequently used.

So - there isn't really a rule. With some verbs, like tell there is a definite tendency for one particular order. But in other contexts it's much more arbitrary. The old rule of "never split an infinitive" is prescriptive rather than descriptive - it doesn't describe the way native speakers actually use the language. However, stylistically, the sentence sometimes seems (to me anyway, but this may be personal) to flow better if the rule is followed.

Hope that helps. If you didn't mean to + infinitive but to as a preposition, then give examples of the sentences you were thinking of and we'll deal with those too

[Prax Cortez]

Hi Sue,

You are right. I meant not+to + infinitive, and thanks for your explanation.

In case of to as a preposition, how do you explain it grammatically?

In the following sentences there are two to’s:

1. I told you “to” not to play that game…
2. I told you “to” not to drive that car…
3. I told you “to” not to come out in public…
4. I told you “to” not to worry!

Questions: 1. Is the use of the first to correct? 2. If the use of the first to is correct, then what is its function in the sentence? 3. If the above sentences are wrong, how do we correct them?

Are the sentences below parallel? Please discuss grammatically.
1. I told you to not to worry - I told you not to worry
2. I told you to not to drive - I told you not to drive
3. I told you to not to come out in public – I told you not to come out in public

I appreciate your extra time and efforts.

[susan53]

I don't know where these examples come from, but if they were written, then they're not correct. The only possibility would be that in spontaneous spoken discourse the person had started a sentence, changed their mind about what they wanted to say, hesitated and corrected themself, thus repeating the to. You can almost imagine it with I mean inserted :

I told you to .... (I mean) not to play that game.

But it's very definitely a repetition - just as if I hesitated and repeated "some" in the following example : We saw some .. some nice houses

But as a "complete" sentence, all your examples 1-4 are ungrammatical. To can't be used twice in that way. As I said in the last reply, it will usually come after the negation (as in the second version of the examples in the second group) : I told you not to play that game etc.

As for prepositions ... Well, in that case not would come in front of the verb, whether the preposition was to or any other. Here are some examples, the first few with random prepositions, the others with to :

Thank you for not saying anything to David.
Do you think I'll offend him by not going.
We're thinking of not having a holiday this year.
He wasn't used to not seeing her
She was committed to not letting it happen again.
Third World bishops objected to not being consulted about Sollicitudo Omnium

The explanation is that the negation always comes before the word or phrase which it negates - here it negates the verb, so is placed in front of the verb. When to+infinitive is used on the other hand, it's seen as a unit - we often think of to as being part of the infinitive. So placing not in front of to still follows the rule that the negation is placed in front of the phrase it negates.

[Prax Cortez]

The sentences with to not to+ infinitive were all mine. I created them for the sake of illustrating the usage.

I knew the sentences were all incorrect, but I didn’t know how to explain the error so I sought help from professionals.

Sue, thanks for your succinct discussion.