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Which of the following sentences is correct, or are they both correct?

I'm not so cold-hearted that I wouldn't reply.
I'm not so cold-hearted as to not reply.

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The choice here is not between "that" and "as to," but simply "as." "As to" is a phrase that means "in the matter of" or "regarding." The second sentence would be broken up as [not so cold-hearted] [as] [to not reply]. –  choster Dec 29 '11 at 15:18
@choster: I disagree. Without the "to" the "as ..." construction becomes simply a comparative, or at least ambiguously so. "I'm not so cold-hearded as [that, you, Kevin, etc.]" — and if used with a verb, it has to be the infinitive (thus mandating to) or else it simply sounds wrong: "I'm not so cold-hearted as not reply [?]" ... –  Robusto Dec 29 '11 at 15:38
It is a comparative. It is equivalent to "I am not so cold-hearted as one who wouldn't reply." That said, I'm not arguing that the "to" can be omitted here, for then the sentence would not even be grammatical, but that the title of the post is misleading. –  choster Dec 29 '11 at 15:40
It is only comparative in an abstract sense. Your example makes a direct comparison between the speaker and a non-specific third party ("one"). The OP's constructions elaborate on a course of action for one person. You can say that these are equivalent, but so are a lot of other things that are not germane to this specific discussion. –  Robusto Dec 29 '11 at 16:08
The construction is not as to (which is not a constituent, I think), but rather A be so X that S vs P be so X as (for P) to VP. The first can be used for anything (X is so tiny that we can't find it), but the second construction requires a volitional subject to be the subject of the infinitive Verb Phrase as well as the Quantified Predicate Adjective (He was even so brave as to take out and wave X at her). The original sentences are weird, though, because they're using double negatives, and they don't always behave the same with different complement types. –  John Lawler Dec 29 '11 at 17:59

2 Answers 2

up vote 6 down vote accepted

Both are completely acceptable and mean essentially the same thing. You can choose based on personal preference or context.

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There appears to be a nuance, making the two sentences quite different in their focus.

I'm not so cold-hearted that I wouldn't reply.

The use of that I returns the focus to I. The speaker is the focus of the sentence. 'Don't think I am that bad.'

I'm not so cold-hearted as to not reply.

The use of the form so[phrase]as concentrates on the [phrase]. Here, cold-hearted is the focus of the sentence. The speaker is not drawing attention to himself but discussing about someone being cold-hearted.

Such constructions are sometimes useful in writing to show what can be expressed in speech by a mere change in the stress.

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