Do regular expressions from the re module support word boundaries (\b)?

Just to explicitly explain why re.search("\btwo\b", x) doesn't work, it's because \b in a Python string is shorthand for a backspace character.

print("foo\bbar")
fobar

So the pattern "\btwo\b" is looking for a backspace, followed by two, followed by another backspace, which the string you're searching in (x = 'one two three') doesn't have.

To allow re.search (or compile) to interpret the sequence \b as a word boundary, either escape the backslashes ("\\btwo\\b") or use a raw string to create your pattern (r"\btwo\b").

This will work: re.search(r"\btwo\b", x)

When you write "\b" in Python, it is a single character: "\x08". Either escape the backslash like this:

"\\b"

or write a raw string like this:

r"\b"

You should be using raw strings in your code

>>> x = 'one two three'
>>> y = re.search(r"\btwo\b", x)
>>> y
<_sre.SRE_Match object at 0x100418a58>
>>> 

Also, why don't you try

word = 'two'
re.compile(r'\b%s\b' % word, re.I)

Output:

>>> word = 'two'
>>> k = re.compile(r'\b%s\b' % word, re.I)
>>> x = 'one two three'
>>> y = k.search( x)
>>> y
<_sre.SRE_Match object at 0x100418850>