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This is one thing that keeps bugging me, and maybe there's a direct answer.

Grammatically, which one is more correct of these two? Does it make a difference?

I tried not to do that.

I tried to not do that.

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4  
The sentence with not between to and the verb (do in this case) is a special case of the split infinitive construction. According to CGEL, 2.3 Secondary verb negation, p. 803, these two sentences are semantically equivalent, and either is acceptable. –  user3286 Apr 29 '11 at 2:30
    
@Vitaly: this sounds like an answer to me -- why not post it as such? –  sibbaldiopsis Apr 29 '11 at 5:57
    
@sibbaldiopsis Because the question itself is a duplicate. There is already a good answer to an earlier question (to which I linked in my previous comment). –  user3286 Apr 29 '11 at 6:14

7 Answers 7

up vote 23 down vote accepted

As some others have said, both are correct, and it is not wrong to say

I tried to not do that.

However, that is not the full story. Searching the Corpus of Contemporary American for various phrases (not to hold vs to not hold; not to know vs to not know; not to go vs to not go) reveals that the not to <verb> form is far more common:

| Verb | Not to <verb> | To not <verb> | %  |
| Hold | 97            | 6             | 94 |
| Know | 1130          | 69            | 94 |
| Go   | 452           | 57            | 88 |

(Note that I didn't search for "not to [any verb]", because that also picks up certain fixed expressions such as "not to mention ..." which might distort the picture.)

So it's clear that the not to <verb> form is far more common. Furthermore, looking at the context of a sample of the to not <verb> examples, most of them appeared to be in speech (either on the radio, or quoted in a magazine), or very informal writing.

Searching the British National Corpus gives an even clearer bias - there, not to <verb> dominates by about 99%.

So in general usage, it is clear that not to <verb> is preferred by most writers.

Why is this? And when should one choose one expression or the other? Naturally this is rather subjective, so take the following explanation as my personal view on the matter, but note that it is consistent with what a lot of other people think.

  • Putting the not in between the to and its verb disrupts the expected flow, creating a slightly jarring effect - the to primes the reader/listener to expect a verb, and so it is a little surprising to find another word there.
  • While the so-called rule against "splitting infinitives" is entirely false, there are nonetheless a sizeable proportion of educated people who believe it is an absolute rule, and will be irritated (or at least, think you poorly educated/stupid) if you do. One should never let this fact scare one into writing awfully clumsy sentences to avoid such disapproval, but in cases where there is nothing to be gained by splitting the infinitive, it's a good idea not to, and that is often the case here.

So when might one want to say to not <verb>?

  • Occasionally this can avoid ambiguity: My aim is not to kill him could either mean I'm not aiming to kill him, or I'm aiming not to kill him. Saying My aim is to not kill him definitely means I'm aiming not to kill him. (In this case I would personally just say I'm aiming not to kill him - but in other circumstances it might not be so easy to rephrase.)
  • As I mentioned in the first bullet point above, putting the not after the to goes against the listener's expectations. This can sometimes be used for effect, especially if you want to put particular emphasis on the not.
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It should sound better to say not + verb rather than to not + verb. e.g.

I try not to tell her all your secret

(I do not try to tell her all your secret).

It looks much more good grammatically than to say

I try to not say all your secret.

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There are so many things wrong with this I don't know where to begin. –  David M Mar 14 at 19:47

Opinion: The word NOT should ALWAYS go before TO + verb. When the emphasis is on not doing something, instead of saying, "I tried to not do that," say, "I tried to avoid doing that." That conveys the same meaning without the split infinitive.

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This sort of rule is commonly stated. It's also importantly wrong in this case. There is a difference between NOT + "to" + [verb of intent] and "to" + NOT + [verb of intent] –  virmaior Feb 11 at 0:59

I think to properly vet this subject one should remember that there are many kinds of verbs (state, event, transitive, etc.). I've seen four possibilities.

  • [nothing]: no infinitive
  • know: base infinitive
  • to know: infinitive
  • knowing: gerund
  1. I know. / I do not know.
  2. I might know. / I might not know.
  3. I would like to know. / I would not like to know. / I would like not to know.
  4. I prefer knowing. / I don't prefer knowing. / I prefer not knowing.

It seems to me most people on this forum are discussing example number three because of the necessity of the word "to". But I think the bigger question is where one puts the blasted negation "not" when confronted with a complex sentence. If it really is a question of emphasis of meaning, it seems to be a very subtle affair, the likes of which make my brain want to turn into mush. It also makes me wonder if the rule of "no double negatives" is grammatically absolute. How is someone like myself supposed to teach this kind of thing to students whose native tongue (French for example) allows for double negatives, as well as only having one infinitive for the three that exist in English? You don't! That's what I say. Blast the complexities of grammar!

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Unless split infinitive is specifically warranted, we ought to go with the natural flow of NOT+TO+VERB.

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Hi, welcome to ELU! This answer would be better with a discussion of the cases where split infinitive is warranted, or why not to verb is more natural. –  Bradd Szonye Apr 23 '13 at 21:30

The normal form of a negative infinitive is "not to X", in all contexts.

The form "to not X" is grammatical (notwithstanding the generations of people who have moaned about "splitting the infinitive"), but unusual, and would only be used in order to convey a special meaning.

So "I try not to care" would be normal, but "I try to not care" would be spoken with an emphasis on the "not", and would suggest that I am trying very hard to do something specific "not caring" instead of caring.

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1  
I think it's well known that any general concern about "splitting the infinitive" with an adverb is a crock, but the construction "to not X" does not sound grammatical to me. It sounds like the speaker of "to not X" is trying to create a new verb "not X" and construe it as a specific verb in a positive sense, which I do not believe is quite correct. So I would say that "to not care" is no more grammatical than its ordinary negation "not to not care", e.g. "I try not to not care" for "I try not to be uncaring. –  JL344 Aug 4 '12 at 21:10
    
Wouldn't the word in front of "not" + infinitive affect this? I'm thinking specifically of the case of "how." Take, for example, "how to not snore" or "how to not drink." That is, asking how to avoid doing the stated action. Although “how not to X” might be used for this, “how to not X” seems more common. But you can also have “how not to X” in which X is something you would or might do, but you’re talking about how to avoid doing it improperly: “how not to speak to your boss,” “how not to dress.” The latter wouldn’t be taken to mean “how to stay naked all day." –  Ascendant Oct 10 '12 at 5:19

Some people will tell you that you should say "I tried not to do that."

However, this is what I think:

When you say, "My goal was to do X," it's clear what that you had a goal and that it was to do X. When you say, "My goal was not to do X," was you goal to ensure that you not do X ("I tried not to do X"), or was doing X just not a goal ("My goal was not to do X but to do Y")? In context it might be clear what you mean based on whether or not you have the "but to do Y" part.

In the example you gave, someone saying that doing "that" simply wasn't a goal of theirs might say "I did not try to do that."

Even if ambiguity does arise, my statement is that you can go right ahead and say "I tried to not do that" if you and your audience are fine with it (or maybe even if your audience isn't fine with it but you choose to ;). In fact, I might recommend it.

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"I tried not to do that" is very unlikely to be interpreted as "I didn't try to do that", because in modern English we don't say "I tried not" to negate "I tried". –  psmears Apr 29 '11 at 9:51

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