Elky talks about these situation on he's book The raisers edge.
"Whenever you decide to check raise in HU play, you must have a definite plan. Sometimes you check raise with the intention of calling an all-in. Other times youíre ready to fold to a shove.
However, itís safe to say that check-raising for information in HU might be one of the most -EV moves, especially against LAGs, hyper-LAGs, and maniacs, because they come over the top too often for your move to be profitable. Therefore, as always, you need to mix up your check raise range among monsters, hands with good showdown value, and complete air. Itís worth noting that raising for information should generally be avoided in nearly all scenarios, as there are often better options.
When you check raise with air, make sure your move actually makes sense. This wonít always be the case on some boards or in some betting sequences. For example, if the board is A-2-3 and you check raise, your range is polarized to very few possible hands (AA, A2, A3, two pair, small sets, and 54) or complete air. If your opponent is observant and picks up on your move, he could call you down with K-high or come over the top.
To determine your patterns of check-raising, you should account for ranges and frequencies, the flow of the game, your opponentís profile, and the level of metagame heís capable of playing. If you check-raise on a bluff, you have to make sure your move is consistent with your pre-flop action and calling range. Going back to the example above, a check raise on a 7-8-9 board is usually much more credible than the same move on the A- 2-3 board, as you might have many more combinations (two pair, upper or lower straight, sets, straight draws, etc.). As a result, it will be much more difficult for your opponent to re-raise you, even with a decent hand.
Check-raises with air should be used with caution, depending on your opponentís profile and how frequently he takes stabs at the pot."
I personally have used this move but I do not recommend doing more than once or twice at a table because good players will fight back at you once they realize what you are doing.
It also works very well in multi way pots where the board is quite dry