How to know that 'to' is infinitive particle or preposition? Which one is correct?

  1. Don't try to be smart.

  2. Don't try to being smart.(is to a preposition?)

  3. Stop trying(is trying a gerund here?) to be smart.

  4. Stop trying to being smart.(is to a preposition?)

Please give reasons also.

3 Answers 3


The verb try can take a "to"-infinitive clause, or a noun clause. It cannot take a prepositional phrase introduced by "to".

This means that your 2 and 4 are not grammatical; your 1 and 3 are: try (whether a base form after don't or a gerund after stop) can take the clause to be smart.

Note that this is a property of try. " ... to being" is not necessarily ungrammatical, if it is in a context that can take a prepositional phrase with "to", eg He is half-way to being smart: "half-way" can take a complement (prepositional phrase) with "to".

  • Can we say Stop trying being smart. Stop try being smart
    – Rocky
    Commented May 5, 2020 at 19:17
  • Try being smart! is fine; so the same with other parts of the verb try (eg He tried being smart). I find Stop trying being smart awkward, because of the two "-ing" words following one another, but it's grammatical as far as I can see. Stop cannot be followed by a base form, so Stop try is not grammatical, whatever follows it.
    – Colin Fine
    Commented May 5, 2020 at 19:22

Examples 2 and 4 are not grammatical, and so can't be analyzed.

In example 1, "to be" is the to-infinitive; "to" is not a preposition.

For example 3, "trying" is a gerund-participle acting as the head of the clause "trying to be smart." That clause is the complement of "stop". The function of "to be" is the same as in example 1.


How to know that 'to' is infinitive particle or preposition?

In an infinitive, the X in to X will be a verb. If it's a preposition, X will be a noun.

Nouns often have articles or other determiners in front of them, if one of these exists for X, to then has to be a preposition.

I walked to the park - the is an article and that only appears in front of nouns.

One thing you can do with verbs here that you can't do with nouns is put an adverb like definitely in between to and X.

I walked to the park - I walked to definitely the park (doesn't work)

I wanted to go - I wanted to definitely go (work).

Also, the only form of a verb that can go after to is the plain form. The -ing or past/past-participle forms can't have to in front of it and make an infinitive.

To walk - might be an infinitive

To walked, to walking - never an infinitive, generally wrong.

Perfect infinitives with to have X'ed are OK; progressive/continuous with to be X'ing is also OK. But to X'ed or to X'ing is not OK.

So 1 and 3 are correct.

You must log in to answer this question.

Not the answer you're looking for? Browse other questions tagged .