I'm currently practising for the TOEFL so I'd really like you to tell me the correct answer for the following question with a brief explanation.
"I spoke to him kindly ...... him."

a) not to frighten
b) so as not to frighten
c) in order to not frighten
d) for not frightening

Only one is correct, so I'd choose a) but nevertheless I actually think d) is possible as well, even though a) sounds better. Since it's just my feeling that tells me to choose either a) or d) I'd appreciate rules eliminating the other options.
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Comments  (Page 3) 
Marius Hancu
Cool Breeze So as normally emphasizes an infinitive. So does in order, but in c) not is in the wrong place. In order not to frighten would be correct.
Tell that to Faulkner or to Shaw (who was quite outspoken about it):Emotion: smile

As I've already mentioned somewhere else here:

Faulkner on Tennyson (in "Light in August"):

It is like listening in a cathedral to an eunuch chanting in a
language which one doesn't even need to not understand.

Hi Marius

I know that there is no Language Academy in the Anglo-Saxon world and rules are based on what reputable writers write. I don't think I can tell Faulkner anything but the fact remains that most authors, and grammarians in particular place not before the entire infinitive to make it negative: to be or not to be, that is the question. Or: you ought not to go.

Hi Na!

In my opinion there is nothing wrong with I spoke kindly to him not to frighten him.

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Hi CB,

In my opinion there is nothing wrong with I spoke kindly to him not to frighten him.
I agree that it's OK, but the 'not' before the infinitive seems to me to weaken a bit the feeling of purpose. Perhaps it's just a bit harder to grasp the idea of a 'negative purpose'?

Consider I spoke kindly to him not to frighten him but to show him that he was safe. Here, you could argue that the 'not to frighten him' does not really express purpose at all.

Best wishes, Clive