Regex: Specify "space or start of string" and "space or end of string"

Imagine you are trying to pattern match "stackoverflow".

You want the following:

 this is stackoverflow and it rocks [MATCH]

 stackoverflow is the best [MATCH]

 i love stackoverflow [MATCH]

 typostackoverflow rules [NO MATCH]

 i love stackoverflowtypo [NO MATCH]

I know how to parse out stackoverflow if it has spaces on both sites using:

/\s(stackoverflow)\s/

Same with if its at the start or end of a string:

/^(stackoverflow)\s/

/\s(stackoverflow)$/

But how do you specify "space or end of string" and "space or start of string" using a regular expression?

You can use any of the following:

\b      #A word break and will work for both spaces and end of lines.
(^|\s)  #the | means or. () is a capturing group. 


/\b(stackoverflow)\b/

Also, if you don't want to include the space in your match, you can use lookbehind/aheads.

(?<=\s|^)         #to look behind the match
(stackoverflow)   #the string you want. () optional
(?=\s|$)          #to look ahead.

(^|\s) would match space or start of string and ($|\s) for space or end of string. Together it's:

(^|\s)stackoverflow($|\s)

Here's what I would use:

 (?<!\S)stackoverflow(?!\S)

In other words, match "stackoverflow" if it's not preceded by a non-whitespace character and not followed by a non-whitespace character.

This is neater (IMO) than the "space-or-anchor" approach, and it doesn't assume the string starts and ends with word characters like the \b approach does.

\b matches at word boundaries (without actually matching any characters), so the following should do what you want:

\bstackoverflow\b