[Grammar] He was very tired...,so he said that he was sorry TO/NOT TO accompany us.

[Sahil Dhankhar]

Disclaimer:-This is not my homework.

He was very tired of work,so he said that he was sorry to accompany us.

I think that as he have not accompanied us due to his tiredness,the sentence should be :- He was very tired of work,so he said that he was sorry not to accompany us.

Please tell me :- Are both the sentences correct and if not then which one is correct? If both are correct, do they have any difference in meaning?

 

[Rover_KE]

Where did you find 'He was very tired of work, so he said that he was sorry to accompany us.'

It's not a natural sentence, even you insert the missing 'not'.

If both are correct, is there any difference in meaning?

Leave a space after every comma.

 

[Sahil Dhankhar]

I found it in a grammar practice book(non-standard).
By the way, thanks for the advice.
Also, please tell :- Does "not" have some significance (even if the sentence is not natural)?

 

[Tarheel]

It is different to say that a person is tired of work rather than to say he is tired from working. A person who is tired of work doesn't want to work anymore. But a person who is tired from working is physically exhausted. A person might say, for example:

I have been working all day, and I need to rest. I am going to stay home for a while.

or

I have been working, and I need to rest. Give me some time, and maybe I'll join you later.

or

I am tired from working. I am going to stay home and rest. Could you bring me some takeout?

or

I've been working a lot, and I'm tired. I'm going to take a nap. But you go out and have fun.

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