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I hear both 残念ながら and 残念なことに when expressing that something was unfortunate
before the actual sentence, much like the English "Unfortunately, ...".

However, I'm not sure on where these two phrases differ. Is their usage the
same?
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question
word-choice grammar usage
What is the difference between 残念ながら and 残念なことに
To me, the two are nigh identical. With `残念ながら` _ever so slightly_ less
formal-sounding (and more common) than `残念なことに`...

According to [this site](http://nihon5ch.net/contents/bbs-study/old/mie-
bbs.cgi?s=118):

> たまたまこの文の場合は、文頭に来る「～ことに」と逆接になる「～ながら」の「～」のところに「残念」という言葉が来ているので、似た用法となっていますね。

Which I roughly interpret as 「〜ことに」giving more surprise/contradiction (but I
must admit I'm not all that clear and could be wholly mistranslating that
one... anybody care to confirm/infirm?).

At any rate, grammar is slightly different:

  * 残念 **なことに** 、抜かなければならない歯は、このような歯です。

  * 残念 **ながら** 抜くことになる歯は このような歯です。
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I believe the difference is:

In `残念ながら` the focus is on the speaker's feeling while they tell you the
information. It's like saying "I'm sorry to have to tell you, but..." The
speaker's feeling of disappointment exists _alongside_ the information.

In `残念なことに`, the focus is on the thing the speaker is telling you, and is a
cause of the disappointment. It's like saying "What's particularly
disappointing is..." The speaker's disappointment _comes from_ the
information.

> 残念ながら、あなたと別れる。 (It's sad, but I'm going to break up with you.)
>
> 残念なことに、結婚しようかなと思っていた。 (What's sad is, I thought we maybe could have
> married.)

These two examples are subtley different. In the in the first case, you are
being told that a breakup will happen, _despite_ the fact the speaker is sad
about it. In the second case, you are being given a fact which is _itself_ a
cause of disappointment.

Hope that helps.
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2011-08-19T07:35:21.667
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I agree with Dave that the two seem very close. If we look at the core
definitions, we can see this:

### 〜ながら: "while 〜"

Although we usually stick this on the end of the verb stem (食べながら、見ながら、など), it
can retain the same meaning in English here.

  * 残念ながら、... → "While it's unfortunate, (here's the truth of it) ..."

### (emotion/feeling word) + ことに(は): "Very 〜", "To my 〜"

  * おどろいたことに → "To my surprise" / "Surprisingly"
  * 嬉しいことに → "Very happily"
  * 残念なことに → "Very unfortunately" / "To my disappointment"
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